Dichloromethane → HCID 69285363, compound

HRID 2223140Notes

Reaction equation

HRID 2223140 reaction equation
BrC[C:3](Cl)=[O:4].[C:6]([NH:10][C:11]([C:13]1[S:34][C:16]2[N:17]=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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[NH2:35])=[O:12])([CH3:9])([CH3:8])[CH3:7].CCN(C(C)C)C(C)C.[CH2:45]([Cl:47])Cl>>[C:6]([NH:10][C:11]([C:13]1[S:34][C:16]2[N:17]=[C:18]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:3](=[O:4])[CH2:45][Cl:47])[CH:22]=3)[C:15]=2[C:14]=1[NH2:35])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 69284083HCID 69284083, compound

Product 1

HCID 69285363HCID 69285363, compound

Procedure

Bromoacetyl chloride (2.80 ml) was added dropwise to a solution of tert-butyl 5-amino-4-(3-aminophenyl)-2-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide (example 9(g), 5.8 g) and DIPEA (12.2 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 1:1 (mol/mol) mixture of tert-butyl 5-amino-4-(3-(2-bromoacetamido)-phenyl)-2-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide and tert-butyl 5-amino-4-(3-(2-chloroacetamido)-phenyl)-2-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide was obtained.

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel
  5. additionA 1:1 (mol/mol) mixture of tert-butyl 5-amino-4-(3-(2-bromoacetamido)-phenyl)-2-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide

Sources & evidence

ORD record
ord-2cd6d90c84874b2fabfe102339054bfc
Source dataset
uspto-grants-2008_05
Patent number
US07375109B2

Reaction notes

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