Thiourea → 4-(2-Amino-4-phenyl-thiazol-5-yl)-2-methylthio-pyrimidine

HRID 2212870Notes

Reaction equation

HRID 2212870 reaction equation
Br[CH:2]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:19][C:20]([NH2:22])=[S:21]>C(O)C>[NH2:22][C:20]1[S:21][C:2]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:19]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 129858302-Bromo-2-[2-(methylthio-4-pyrimidinyl)]-1-phenylethanone

Product 1

HCID 219559554-(2-Amino-4-phenyl-thiazol-5-yl)-2-methylthio-pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone (45 g, 0.14 mol) and thiourea (21.2 g, 0.28 mol) in ethanol (300 ml) is heated at reflux for 4 hours. On cooling the product starts to crystallize as salt. It is filtered with suction and washed with ether. The free amine is obtained by partitioning of the product between an aqueous solution of sodium bicarbonate and a 1:1 mixture of ethyl acetate and tetrahydrofuran, followed by drying of the organic phase over magnesium sulfate, filtering and evaporation of the solvents. The 4-(2-amino-4-phenyl-thiazol-5-yl)-2-methylthio-pyrimidine is obtained in crystalline form, m.p. 208–209° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureOn cooling the product
  3. customto crystallize as salt
  4. filtrationIt is filtered with suction
  5. washwashed with ether

Sources & evidence

ORD record
ord-38bff30b45da4d7aa60d0bd4b4b018b1
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

Loading…