Dichloromethane → HCID 69286296, compound

HRID 2223141Notes

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.

Workup

washwashed with sat. aq. NaHCO3
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customThe crude product was purified by chromatography on silica gel
additionA mixture of tert-butyl 5-amino-4-(3-(2-bromoacetamido)-phenyl)-2-(2-thienyl)-thieno[2,3-d]pyrimidine-6-carboxamide

Sources & evidence

ORD record: ord-3ab6435517ab4d5eb56fa97ce493eda1
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375109B2

Reaction notes

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