Trifluoroacetic acid → 1,4,5,6-Tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine trifluoroacetate

HRID 1653712Notes

Reaction equation

HRID 1653712 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH2:13][CH:12]([C:14]3[O:18][N:17]=[C:16]([CH3:19])[N:15]=3)[CH2:11][N:10]=[CH:9]2)C=CC=CC=1.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[CH3:19][C:16]1[N:15]=[C:14]([CH:12]2[CH2:13][NH:8][CH:9]=[N:10][CH2:11]2)[O:18][N:17]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 100244281-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

Product 1

HCID 98385801,4,5,6-Tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine trifluoroacetateYield 62%

Procedure

1-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine (254 mg, 0.6 mmol) is dissolved in trifluoroacetic acid (TFA) (1 mL) with stirring at room temperature for 24 hours. The dark solution is then evaporated in vacuo, and the residue recrystallized from methanol/ether to yield 105 mg (62%) white crystals, mp 120°-122° C. identified by 300 MHz nmr. Calculated: C 38.57, H 3.96, N 19.99; found: C 38.72, H 4.09, N 19.78.

Workup

  1. customThe dark solution is then evaporated in vacuo
  2. customthe residue recrystallized from methanol/ether

Sources & evidence

ORD record
ord-7b6b6c7fcb484780847907858e330cb0
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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