Potassium Carbonate → Phenyl 4-(trifluoromethyl)pyrimidin-2-ylcarbamate

HRID 871492Notes

Reaction equation

HRID 871492 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>O1CCCC1>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformate2×HCID 5959152-Amino-4-(trifluoromethyl)pyrimidine

Product 1

HCID 23212816Phenyl 4-(trifluoromethyl)pyrimidin-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure described in Example 113B, to a solution of 4-(trifluoromethyl)pyrimidin-2-amine (500 mg, 3.1 mmoles) in 20 mL of tetrahydrofuran was added potassium carbonate (533 mg, 4 mmoles) followed by phenyl chloroformate (626 mg, 4 mmoles). The mixture was stirred at room temperature overnight. After 24 hours, and additional portion of phenyl chloroformate was added and the reaction heated to 60° C. for 3 days. This solution was concentrated to dryness and purified by silica chromatography (eluted with a gradient of 0-5% ethyl acetate/dichloromethane) to afford phenyl 4-(trifluoromethyl)pyrimidin-2-ylcarbamate. 1H NMR (300 MHz, DMSO-d6) δ 11.50 (s, 1H), 9.05 (s, 1H), 7.69 (m, 1H), 7.46 (m, 2H), 7.25 (m, 3H).

Workup

  1. waitAfter 24 hours
  2. temperaturethe reaction heated to 60° C. for 3 days
  3. concentrationThis solution was concentrated to dryness
  4. custompurified by silica chromatography (
  5. washeluted with a gradient of 0-5% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-d28ebb43954b42bdb362c8e5692e0214
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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