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

HRID 2098622ノート

反応式

HRID 2098622 の反応式
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

参加物

7

反応物 4

HCID 10340Sodium Carbonate2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ce22b7a2214c4312a96bdf09a376fe5d
出典データセット
uspto-grants-2013_05
特許番号
US08450315B2

反応ノート

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