홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Ammonia → 4-[4-amino-5-(4-amino-3-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclohexanone

HRID 51567
노트
인쇄 미리보기

반응식

HRID 51567 반응식
N.O1CCOCC1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([CH:25]3[CH2:34][CH2:33][C:28]4(OCC[O:29]4)[CH2:27][CH2:26]3)[CH:16]=2)=[CH:11][C:10]=1[O:35][CH3:36].Cl>CC(C)=O>[NH2:24][C:22]1[C:23]2[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH2:8])=[C:10]([O:35][CH3:36])[CH:11]=3)=[CH:16][N:17]([CH:25]3[CH2:34][CH2:33][C:28](=[O:29])[CH2:27][CH2:26]3)[C:18]=2[N:19]=[CH:20][N:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 227364215-(4-Amino-3-methoxyphenyl)-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 227363904-[4-amino-5-(4-amino-3-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclohexanone수율 78%

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

tert-Butyl N-4-[4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-methoxyphenylcarbamate (5.7 g, 0.011 mol), conc. ammonia solution (100 mL) and dioxan (100 mL) were heated in a pressure vessel for 20 hr at 120° C. The solvent was evaporated and the residue reconstituted in EtOAc/water (250 mL/100 mL). The organic layer was separated , dried (sodium sulphate), filtered and evaporated to give a solid which by HPLC (conditions: 5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min.) was observed to be a 2:1 mixture of tert-butyl N-4-[4-amino-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-methoxyphenylcarbamate and 5-(4-amino-3-methoxyphenyl)-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine. The mixture was dissolved in acetone (200 mL) and HCl (SN, 100 mL) was added dropwise over 0.5 hr. The resulting solution was stirred at room temperature overnight and the solvent was then evaporated. The acidic solution was basified with 2N NaOH (ice-cooling) and extracted with EtOAc (3×150 mL). The combined organics were washed with water (2×100 mL). During the extraction process a solid precipitated. This solid was filtered and triturated in hot EtOAc/MeOH. The insolubles were filtered, the filtrate evaporated and then resulting solid triturated with diethylether/ethyl acetate to give a yellow solid. The organic layers from the original extraction were dried (sodium sulphate), filtered and evaporated. The resulting solid was triturated with diethyl ether/ethyl acetate (5:1) and filtered to give 4-[4-amino-5-(4-amino-3-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclohexanone as a yellow solid. (2.3 g, combined yield=78%). 1H NMR (d6 DMSO, 400 MHz): 8.17(1H, s), 7.32(1H, s), 6.88(1H, s), 6.77(1H, m), 6.73(1H, m), 6.71(1H, m), 6.07(2H, bs), 5.14(1H, m), 3.81 (3H, s), 2.72(2H, m), 2.35(4H, m), 2.18 (2H, m). HPLC: (5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min.) tr=11.24 min, 95%

후처리

  1. customThe solvent was evaporated
  2. customThe organic layer was separated
  3. dry with materialdried (sodium sulphate)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a solid which by HPLC (conditions: 5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min.)
  7. customthe solvent was then evaporated
  8. extractionextracted with EtOAc (3×150 mL)
  9. washThe combined organics were washed with water (2×100 mL)
  10. customDuring the extraction process a solid precipitated
  11. filtrationThis solid was filtered
  12. customtriturated in hot EtOAc/MeOH
  13. filtrationThe insolubles were filtered
  14. customthe filtrate evaporated
  15. customresulting solid
  16. customtriturated with diethylether/ethyl acetate
  17. customto give a yellow solid
  18. extractionThe organic layers from the original extraction
  19. dry with materialwere dried (sodium sulphate)
  20. filtrationfiltered
  21. customevaporated
  22. customThe resulting solid was triturated with diethyl ether/ethyl acetate (5:1)
  23. filtrationfiltered

출처 및 근거

ORD 기록
ord-e81fe03e478b4d3bbbaee2372386b2f7
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06713474B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트