Sodium hydride → 4-amino-5-(4-phenoxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 51480

반응식

HRID 51480 반응식
[H-].[Na+].[NH2:3][C:4]1[C:5]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1.S(O[CH:37]1[CH2:41][CH2:40][O:39][CH2:38]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[O:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]2[C:5]3[C:4]([NH2:3])=[N:9][CH:8]=[N:7][C:6]=3[N:10]([CH:37]3[CH2:41][CH2:40][O:39][CH2:38]3)[CH:11]=2)=[CH:18][CH:17]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamineHCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonate

생성물 1

HCID 227363324-amino-5-(4-phenoxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
95 °C

실험 절차

Sodium hydride (120 mg, of a 60% dispersion in mineral oil) was added to a solution of 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (906 mg) and dimethylformamide (30 ml) with stirring under nitrogen. The mixture was stirred for 30 minutes and then a solution of 3-(tosyloxy) tetrahydrofuran (750 mg) in dimethyl formamide (10 ml) was added with stirring. The mixture was stirred and heated at 95° C. for 18 hours and then evaporated under vacuum. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried and evaporated to give a residual gummy solid which was triturated with ether and filtered to give 5-(4-phenoxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine m.p. 196-196.5° C.

후처리

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringwith stirring
  3. stirringThe mixture was stirred
  4. customevaporated under vacuum
  5. customThe residue was partitioned between ethyl acetate and water
  6. customThe ethyl acetate layer was separated
  7. customdried
  8. customevaporated
  9. customto give a residual gummy solid which
  10. customwas triturated with ether
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-7a4d91e2f8894e729bbc93864baa2b96
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713474B2

연결된 노트

불러오는 중…