Diisopropylethylamine → HCID 86603171, compound

HRID 1818938Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[CH3:15])=[O:4].[NH2:16][CH2:17][CH2:18][C:19]1[S:23][C:22]([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)=[O:26])=[N:21][CH:20]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH4:1].[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:16][CH2:17][CH2:18][C:19]3[S:23][C:22]([NH:24][C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:36])([F:37])[F:35])[CH:29]=4)=[O:26])=[N:21][CH:20]=3)[C:7]=2[C:6]=1[CH3:15])=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

A 20 mL vial was charged with 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (250 mg, 100 mol %), compound 38.1 (341 mg, 100 mole %), DIEA (1 mL) and DMF (2 mL). The resulting suspension was heated at 110° C. for 2 hours and cooled to room temperature. Concentration in vacuo provided 5-methyl-4-(2-{2-[3-(3-trifluoromethyl-phenyl)-ureido]-thiazol-5-yl}-ethylamino)-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester; compound with methane (compound 43.1) as a solid that was used in the next reaction without further purification. LCMS [M+H]+ m/z 537.2

Workup

temperaturecooled to room temperature
concentrationConcentration in vacuo

Sources & evidence

ORD record: ord-52917d22f297408f850f1d4f7ef290c7
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601725B2

Reaction notes

Loading…