1,1,1-Trifluoro-2-isothiocyanatoethane → 4-[3-(2,2,2-Trifluoroethyl)thioureido]-2-(4-phthalimidobut-2-ynylthio)pyrimidine

HRID 542481Notes

Reaction equation

HRID 542481 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][C:10]#[C:11][CH2:12][N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])[N:3]=1.[F:24][C:25]([F:31])([F:30])[CH2:26][N:27]=[C:28]=[S:29]>CN(C=O)C>[F:24][C:25]([F:31])([F:30])[CH2:26][NH:27][C:28](=[S:29])[NH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][C:10]#[C:11][CH2:12][N:13]2[C:14](=[O:23])[C:15]3=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]3[C:17]2=[O:18])[N:3]=1

Participants

4

Reactant 2

HCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 202087134-Amino-2-(4-phthalimidobut-2-ynylthio)pyrimidine

Product 1

HCID 540628734-[3-(2,2,2-Trifluoroethyl)thioureido]-2-(4-phthalimidobut-2-ynylthio)pyrimidineYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-2-(4-phthalimidobut-2-ynylthio)pyrimidine (1.2 g.), 2,2,2-trifluoroethylisothiocyanate (0.85 g.) and DMF (10 ml.) was stirred at 70° for 72 hours. The mixture was evaporated to dryness, and the residue stirred with N aqueous HCl and then filtered to give 4-[3-(2,2,2-trifluoroethyl)thioureido]-2-(4-phthalimidobut-2-ynylthio)pyrimidine (0.4 g.), m.p. 124°-127°.

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringthe residue stirred with N aqueous HCl
  3. filtrationfiltered

Sources & evidence

ORD record
ord-78e6cce336b14430a39fde6900b94eba
Source dataset
uspto-grants-1987_04
Patent number
US04657908

Reaction notes

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