Dichloromethane → 2-Amino-4-{2,4-Dichloro-5-[2-(Diethylamino)ethoxy]phenyl}-N-Ethylthieno[2,3-D]pyrimidine-6-Carboxamide

HRID 1161736Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16]=[C:17]([NH2:29])[N:18]=[C:19]([C:20]3[CH:25]=[C:24]([OH:26])[C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[C:14]=2[CH:13]=1)=[O:11])[CH3:8].ClCCl.Br.Br[CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40]>CN(C=O)C>[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16]=[C:17]([NH2:29])[N:18]=[C:19]([C:20]3[CH:25]=[C:24]([O:26][CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[C:14]=2[CH:13]=1)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 140 °C

Procedure

Cesium carbonate was added to a solution of 2-Amino-4-(2,4-dichloro-5-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide in DMF, 2-Bromo-N,N-diethylethylamine hydrobromide was added and the suspension heated, at ˜140° C., for ˜2 hrs. The resulting suspension was allowed to cool and dichloromethane added. The mixture was washed with water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a dark brown gum. The crude product was purified by chromatography on silica eluting with mixtures of dichloromethane and methanol.

Workup

additionwas added
temperatureto cool
washThe mixture was washed with water and saturated aqueous sodium chloride solution
dry with materialThe solution was dried over anhydrous sodium sulphate
concentrationconcentrated to a dark brown gum
customThe crude product was purified by chromatography on silica eluting with mixtures of dichloromethane and methanol

Sources & evidence

ORD record: ord-5693b8171b454354af0c79c5387ba015
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820658B2

Reaction notes

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