Dichloromethane → HCID 69286296, compound

Reaction equation

BrC[C:3](Cl)=[O:4].[C:6]([NH:10][C:11]([C:13]1[S:33][C:16]2[N:17]=[C:18]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=3)[C:15]=2[C:14]=1[NH2:34])=[O:12])([CH3:9])([CH3:8])[CH3:7].CCN(C(C)C)C(C)C.[CH2:44]([Cl:46])Cl>>[C:6]([NH:10][C:11]([C:13]1[S:33][C:16]2[N:17]=[C:18]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:3](=[O:4])[CH2:44][Cl:46])[CH:22]=3)[C:15]=2[C:14]=1[NH2:34])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

Reactant 4

HCID 6344Dichloromethane2×

HCID 81531Diisopropylethylamine

HCID 89602Bromoacetyl chloride

HCID 69284084HCID 69284084, compound

Product 1

HCID 69286296HCID 69286296, compound

Procedure

Bromoacetyl chloride (2.40 ml) was added to a solution of tert-butyl 5-amino-4-(3-aminophenyl)-2-(2-thienyl)-thieno[2,3-d]pyrimidine-6-carboxamide (example 14(g), 5.0 g) and DIPEA (10.5 ml) in DCM (50 ml). After 3 h at room temperature, the mixture was diluted with DCM, washed with sat. aq. NaHCO3, dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel using heptane/EtOAc=3/2 (v/v) as eluent. A mixture of tert-butyl 5-amino-4-(3-(2-bromoacetamido)-phenyl)-2-(2-thienyl)-thieno[2,3-d]pyrimidine-6-carboxamide and tert-butyl 5-amino-4-(3-(2-chloroacetamido)-phenyl)-2-(2-thienyl)-thieno[2,3-d]pyrimidine-6-carboxamide was obtained.