Cyanamide → Cyanamide, [2-(methylthio)-4-pyrimidinyl]-

HRID 544574Notes

Reaction equation

HRID 544574 reaction equation
[N:1]#[C:2][NH2:3].CC(C)([O-])C.[K+].N#CN.[K].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1>CN(C=O)C>[C:2]([NH:3][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1)#[N:1]

Participants

6

Reactant 4

HCID 9864CyanamideHCID 971134-Chloro-2-methylthiopyrimidineHCID 23665647Potassium tert-butoxideHCID 8673943220611-80-7

Product 1

HCID 20458209Cyanamide, [2-(methylthio)-4-pyrimidinyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyanamide (1.05 g.) was added to potassium t-butoxide (2.8 g.) in DMF (10 ml.) with stirring to produce a fine suspension of potassium cyanamide. To this was added 4-chloro-2-methylthiopyrimidine (4 g.) and the mixture stirred at ambient temperature for 17 hours. The DMF was evaporated in vacuo and the residue suspended in water (20 ml.), the pH adjusted to 11 with dilute aqueous sodium hydroxide and the mixture extracted with EtOAc (2×10 ml.). The aqueous layer was separated, acidified to pH 3 with dilute hydrochloric acid and the precipitate collected, washed with water and dried to give 4-cyanoamino-2-methylthiopyrimidine, m.p. 189-191 (decomp.).

Workup

  1. customto produce
  2. stirringthe mixture stirred at ambient temperature for 17 hours
  3. customThe DMF was evaporated in vacuo
  4. extractionthe mixture extracted with EtOAc (2×10 ml.)
  5. customThe aqueous layer was separated
  6. customthe precipitate collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-8dadc2229bbf4f4ba3ff64a9a3c06952
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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