Potassium Carbonate → 4-(2-Cyclobutoxy-4-fluoro-phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 406104Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:22][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[OH:21])[C:7]=2[C:6]=1[CH3:23])=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:31]1[CH2:34][CH2:33][CH2:32]1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:22][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[O:21][CH:31]3[CH2:34][CH2:33][CH2:32]3)[C:7]=2[C:6]=1[CH3:23])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(4-fluoro-2-hydroxy-phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (200 mg), potassium carbonate (166 mg) and bromocyclobutane (113 μl) in DMF (3 ml) was stirred at 60° C. over the weekend. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was concentrated and the residue was triturated with diethyl ether to give the desired compound.

Workup

washwashed with water and brine
concentrationThe organic layer was concentrated
customthe residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-1088eb0a6b9e4ff8af0405e32c9375a3
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754079B2

Reaction notes

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