2-Chloropyrimidine → N-(2-aminophenyl)-5-pyrimidin-2-yl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

HRID 2093076Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:19][C:20]2[CH2:21][NH:22][CH2:23][CH2:24][C:25]=2[N:26]=1)=[O:17]>CN(C=O)C>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:19][C:20]2[CH2:21][N:22]([C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:23][CH2:24][C:25]=2[N:26]=1)=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro pyrimidine (1.2 eq) in DMF, N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide obtained from step VIII of example I (1.0 eq) was added and the reaction mixture was stirred at 100° C. for 15 h. Solvent was then evaporated under reduced pressure to afford crude product, which, on purification by column chromatography or preparative HPLC afforded the title compound.

Workup

customSolvent was then evaporated under reduced pressure
customto afford crude product, which
customon purification by column chromatography or preparative HPLC

Sources & evidence

ORD record: ord-2a70e22399a64089b1d096769668adb6
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440830B2

Reaction notes

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