5-Bromopyrimidine → 6-Methyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (4-cyclopropyl-thiazol-2-yl)-amide
Reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]([NH:9][C:10]([C:12]3[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([CH3:19])[N:13]=3)=[O:11])[S:7][CH:8]=2)[CH2:3][CH2:2]1.Br[C:21]1[CH:22]=[N:23][CH:24]=[N:25][CH:26]=1>[Pd]>[CH:1]1([C:4]2[N:5]=[C:6]([NH:9][C:10]([C:12]3[C:17]([NH:18][C:21]4[CH:22]=[N:23][CH:24]=[N:25][CH:26]=4)=[CH:16][CH:15]=[C:14]([CH3:19])[N:13]=3)=[O:11])[S:7][CH:8]=2)[CH2:2][CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The tide compound was prepared from 3-tert-Butoxy-carbonylamino-6-methyl-pyridine-2-carboxylic acid methyl ester in accordance with the general method of example 4; step 2 using 4-Cyclopropyl-thiazol-2-ylamine instead of 2-chloro-4-aminopyridine to yield [2-(4-Cyclopropyl-thiazol-2-ylcarbamoyl)-6-methyl-pyridin-3-yl]-carbamic acid tert-butyl ester as a yellow solid, MS (ISP): m/e=375.4 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (4-cyclopropyl-thiazol-2-yl)-amide as a yellow solid, MS (ISP): m/e=275.1 (M+H+). Palladium catalysed arylation in accordance with the general method of example 20, using 5-Bromopyrimidine instead of 3bromopyridine yielded the final compound as a light yellow solid, MS (ISP): m/e=357.1 (M+H+).
Sources & evidence
- ORD record
- ord-7556e4e5fcd844389444a3b7b1ae7c69
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414060B2
Reaction notes
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