5-Bromopyrimidine → HCID 11587901, compound

HRID 2219530Notes

Reaction equation

HRID 2219530 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([NH:7][C:8]([C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([CH3:17])[N:11]=2)=[O:9])[N:6]=1.Br[C:19]1[CH:20]=[N:21][CH:22]=[N:23][CH:24]=1>[Pd]>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([NH:7][C:8]([C:10]2[C:15]([NH:16][C:19]3[CH:20]=[N:21][CH:22]=[N:23][CH:24]=3)=[CH:14][CH:13]=[C:12]([CH3:17])[N:11]=2)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 783445-BromopyrimidineHCID 86607586HCID 86607586, compound

Product 1

HCID 11587901HCID 11587901, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title 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-amino-2-methylthiazole (CAS: [103392-01-4], European Patent EP 321115) instead of 2-chloro-4-aminopyridine to yield [6-Methyl-2-(2-methyl-thiazol-4-ylcarbamoyl)-pyridin-3-yl]-carbamic acid tert-butyl ester as a light yellow cristalline solid, MS (ISP): m/e=349.0 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (2-methyl-thiazol-4-yl)-amide as a light yellow cristalline solid, MS (ISP): m/e=249.1 (M+H+). Palladium catalysed arylation with 5-bromopyrimidine as described in example 20 yielded the final compound as an off-white crystalline solid, MS (ISP): m/e=327.0 (M+H+).

Sources & evidence

ORD record
ord-30deb680fe664a3fac8cff57d7fcf94a
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

Loading…