Potassium Carbonate → 5-(1-methyl-1H-pyrazol-5-yl)pyrimidine-2-carboxylic acid

HRID 2196402Notes

Reaction equation

[CH3:1][N:2]1[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=[N:3]1.C([O-])([O-])=O.[K+].[K+].Br[C:23]1[CH:24]=[N:25][C:26]([C:29]([OH:31])=[O:30])=[N:27][CH:28]=1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]1[C:6]([C:23]2[CH:24]=[N:25][C:26]([C:29]([OH:31])=[O:30])=[N:27][CH:28]=2)=[CH:5][CH:4]=[N:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.35 g, 6.5 mmol) in dioxane/H2O (5:1, 59 mL) was added K2CO3 (2.8 g, 20.3 mmol), tetrakistriphenylphosphine Pd(0) (340 mg, 0.3 mmol), and 5-bromo-2-pyrimidinecarboxylic acid (1.2 g, 5.9 mmol). The reaction mixture was heated to 80° C. in a sealed tube for 12 h. The reaction solution was poured onto H2O (100 mL) and extracted with DCM. The organics were dried (Na2SO4), concentrated under vacuum to give the title compound (0.9 g, 36%) as a tan solid: LC-MS (ES) m/z=437 (M+H)+.

Workup

additionThe reaction solution was poured onto H2O (100 mL)
extractionextracted with DCM
dry with materialThe organics were dried (Na2SO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-d3356a7b41aa466599c252170fe17002
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338434B2

Reaction notes

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