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

HRID 2196402
Notes
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Reaction equation

HRID 2196402 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 164629705-Bromopyrimidine-2-carboxylic acid

Product 1

HCID 593549905-(1-methyl-1H-pyrazol-5-yl)pyrimidine-2-carboxylic acidYield 74.7%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 218864351,4-Dioxane--water (1/1)Solvent

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

  1. additionThe reaction solution was poured onto H2O (100 mL)
  2. extractionextracted with DCM
  3. dry with materialThe organics were dried (Na2SO4)
  4. 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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