Cesium carbonate → 5-(2-Ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

HRID 1922764

反応式

HRID 1922764 の反応式
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH2:17]([C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1)[CH3:18].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:17]([C:19]1[N:20]([C:2]2[N:3]=[C:4]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=2)[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1)[CH3:18]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 158072-EthylbenzimidazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 576853854-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine

生成物 1

HCID 596056325-(2-Ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

A mixture of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine (3.0 g, 11.7 mmol), 2-ethylbenzimidazole (1.88 g, 12.9 mmol), tris(dibenzylideneacetone)dipalladium (534 mg, 0.60 mmol), XPhos (1.11 g, 2.34 mmol) and Cs2CO3 (7.62 g, 23 4 mmol) in dioxane (60 mL) was purged with argon then heated at 120° C. for 16 h in a sealed tube. The reaction mixture was filtered through Celite®, and the filtrated partitioned between EtOAc and H2O. The organic phase was washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 0-90%) followed by recrystallisation from iPrOAc affording the title compound (3.17 g, 74%). LCMS (method A): RT 2.74 min [M+H]+ 367.1

後処理

  1. customwas purged with argon
  2. filtrationThe reaction mixture was filtered through Celite®
  3. customthe filtrated partitioned between EtOAc and H2O
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 0-90%)
  8. customfollowed by recrystallisation from iPrOAc affording the title compound (3.17 g, 74%)
  9. customRT 2.74 min [M+H]+ 367.1

出典と根拠

ORDレコード
ord-fd29f7bce32b42da9ab4fcda52cd0e0d
出典データセット
uspto-grants-2012_05
特許番号
US08173650B2

関連ノート

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