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

HRID 1681879Notes

Reaction equation

HRID 1681879 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-1315face5e334b55ac695ac785891878
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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