Dimethylformamide → 4-[3-(2,2,2-Trifluoroethyl)thioureido]-2-(2-phthalimidoethylthio)pyrimidine

HRID 1902300Notes

Reaction equation

HRID 1902300 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])[N:3]=1.[F:22][C:23]([F:29])([F:28])[CH2:24][N:25]=[C:26]=[S:27].CN(C)C=O>C(#N)C>[F:22][C:23]([F:29])([F:28])[CH2:24][NH:25][C:26](=[S:27])[NH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 212987374-Amino-2-(2-phthalimidoethylthio)pyrimidine

Product 1

HCID 538952134-[3-(2,2,2-Trifluoroethyl)thioureido]-2-(2-phthalimidoethylthio)pyrimidineYield 59.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-amino-2-(2-phthalimidoethylthio)pyrimidine (0.8 g.), 2,2,2-trifluoroethylisothiocyanate (0.56 g.) and dimethyl formamide (2 ml.) was stirred at 70° for 72 hours. The mixture was cooled, diluted with acetonitrile and filtered to give 4-[3-(2,2,2-trifluoroethyl)thioureido]-2-(2-phthalimidoethylthio)pyrimidine (0.7 g.), m.p. 238°-241°.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-418e5f0f7b334b7589c39d44c01750ce
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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