Ammonia → 4-[2-(2,2,2-Trifluoroethyl)-guanidino]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine

HRID 1902272Notes

Reaction equation

HRID 1902272 reaction equation
[F:1][C:2]([F:30])([F:29])[CH2:3][NH:4][C:5](=S)[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[N:8]=1.[NH3:31]>CN(C)C=O>[F:1][C:2]([F:30])([F:29])[CH2:3][N:4]=[C:5]([NH2:31])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 538482754-[3-(2,2,2-Trifluoroethyl)thioureido]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine

Product 1

HCID 212987504-[2-(2,2,2-Trifluoroethyl)-guanidino]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[3-(2,2,2-trifluoroethyl)-thioureido]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine (6.8 g.), dimethylformamide (30 ml.), saturated ethanolic ammonia (5 ml.) and yellow mercuric oxide (6.5 g.) was stirred at room temperature for 2 hours and then filtered. The filtrate was evaporated to dryness and the residue triturated with ether and filtered to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine (5.6 g.), m.p. 167°-168° after crystallisation from ethanol.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. customthe residue triturated with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-cb33b673e4334f67bcb0fb20fbf8c295
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

Loading…