Sodium Carbonate → 2-(1H-Indazol-4-yl)-6-(3-(methylsulfonyl)phenyl)-4-morpholinofuro[3,2-d]pyrimidine

HRID 2098622노트

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HRID 2098622 반응식
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[O:10][C:9](I)=[CH:8][C:6]=2[N:7]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20].C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:45]2[CH:53]=[CH:52][CH:51]=[C:50]3[C:46]=2[CH:47]=[N:48][NH:49]3)O1>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:49]1[C:50]2[C:46](=[C:45]([C:2]3[N:3]=[C:4]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)[C:5]4[O:10][C:9]([C:26]5[CH:25]=[CH:24][CH:23]=[C:22]([S:19]([CH3:18])(=[O:21])=[O:20])[CH:27]=5)=[CH:8][C:6]=4[N:7]=3)[CH:53]=[CH:52][CH:51]=2)[CH:47]=[N:48]1

참가 물질

7

반응물 4

HCID 10340Sodium Carbonate2회HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595930702-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine

생성물 1

HCID 595928562-(1H-Indazol-4-yl)-6-(3-(methylsulfonyl)phenyl)-4-morpholinofuro[3,2-d]pyrimidine

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매2회HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

2-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine (40 mg, 1.0 eq) was dissolved in acetonitrile (0.4 ml) and treated with 3-(methylsulfonyl)phenylboronic acid (23 mg, 1.05 eq), PdCl2(PPh3)2 (7.7 mg, 0.10 eq) and 1M Na2CO3 (0.33 ml). The vial was sealed and heated with stirring in the microwave to 100° C. for 30 minutes. Reaction mixture was quenched with saturated aq. NaHCO3 and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The residue was dissolved in acetonitrile (0.4 ml) and treated with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (53 mg, 2.0 eq), PdCl2(PPh3)2 (7.7 mg, 0.10 eq) and 1M Na2CO3 (0.33 ml). The vial was sealed and heated with stirring in the microwave to 150° C. for 15 minutes. The crude reaction mixture was concentrated and purified by reverse phase HPLC to afford 2-(1H-indazol-4-yl)-6-(3-(methylsulfonyl)phenyl)-4-morpholinofuro[3,2-d]pyrimidine 111 MS (Q1) 476 (M)+.

후처리

  1. customThe vial was sealed
  2. temperatureheated
  3. customReaction mixture
  4. customwas quenched with saturated aq. NaHCO3
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in acetonitrile (0.4 ml)
  9. customThe vial was sealed
  10. temperatureheated
  11. stirringwith stirring in the microwave to 150° C. for 15 minutes
  12. customThe crude reaction mixture
  13. concentrationwas concentrated
  14. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-ce22b7a2214c4312a96bdf09a376fe5d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450315B2

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