4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 67429987, compound

HRID 2036286Notes

Reaction equation

HRID 2036286 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.CCN(C(C)C)C(C)C.[CH3:24][N:25]1[CH:29]=[CH:28][C:27]([NH2:30])=[N:26]1>C1COCC1>[CH3:24][N:25]1[CH:29]=[CH:28][C:27]([NH:30][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=2)=[N:26]1

Participants

5

Reactant 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazole

Product 1

HCID 67429987HCID 67429987, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 800 mg of ethyl 4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxylate in 20 mL of THF, 890 mg of DIPEA and 368 mg of 1-methyl-1H-pyrazol-3-amine were added, and the resulting mixture was stirred under reflux for 2 hours, and then, the solvent was distilled off. The thus obtained crude product was purified by silica gel column chromatography, whereby 820 mg the title compound was obtained.

Workup

  1. temperatureunder reflux for 2 hours
  2. distillationthe solvent was distilled off
  3. customThe thus obtained crude product
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f1cd5f872e0849eeb3f6e024b985d9bd
Source dataset
uspto-grants-2013_11
Patent number
US08575179B2

Reaction notes

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