Toluene → Ethyl 2-(pyrimidinylamino)-4-(trifluoromethyl)-5-oxazolecarboxylate

HRID 619882Notes

Reaction equation

HRID 619882 reaction equation
C1(C)C=CC=CC=1.Cl[C:9]1[O:10][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=1.[NH2:23][C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1>C(OCC)C>[N:25]1[CH:26]=[CH:27][CH:28]=[N:29][C:24]=1[NH:23][C:9]1[O:10][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 79782-AminopyrimidineHCID 12785855Ethyl 2-chloro-4-(trifluoromethyl)oxazole-5-carboxylate

Product 1

HCID 14672733Ethyl 2-(pyrimidinylamino)-4-(trifluoromethyl)-5-oxazolecarboxylateYield 63.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A reaction vessel was charged with 50 ml toluene, 4 g (16.4 mmol) ethyl 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate and 3.12 g (32.8 mmol) 2-aminopyrimidine. The reaction mixture was heated at a temperature of 100°-110° C. for 16 hours. The mixture was cooled to room temperature, diluted with ethyl ether, washed with 5% hydrochloric acid, and then washed with large amounts of water. The ether portion was dried over magnesium sulfate and then concentrated under reduced pressure to yield 3.14 g of a yellow oily-solid material. This material was recrystallized from an ethanol-water solution to provide a yellow solid material which was air dried at room temperature, then triturated in warm hexane, and finally recrystallized from ethanol-water solution to yield 2.06 g of a yellow solid material (m.p. 199°-205° C.) identified in Table I.

Workup

  1. temperatureThe reaction mixture was heated at a temperature of 100°-110° C. for 16 hours
  2. washwashed with 5% hydrochloric acid
  3. washwashed with large amounts of water
  4. dry with materialThe ether portion was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8dbd46e70f9d49e19d34dc365de7d4c0
Source dataset
uspto-grants-1989_04
Patent number
US04818270

Reaction notes

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