Ammonia → 2-(Methylthio)pyrimidin-4-amine

HRID 16247

Reaction equation

HRID 16247 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[NH3:10]>CO>[CH3:9][S:8][C:4]1[N:3]=[C:2]([NH2:10])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 2592252-(Methylthio)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-2-methylsulfanylpyrimidine (8 g) and 7N ammonia in methanol (100 mL) at 100° C. was stirred for 2 days in a sealed tube, cooled, concentrated, treated with water, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The concentrate was triturated with ethyl ether and filtered. 1H NMR (300 MHz, CDCl3) δ 8.06 (d, 1H), 6.12 (d, 1H), 4.83 (s, 2H), 2.51 (s, 3H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. additiontreated with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was triturated with ethyl ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-ee4c67b25ee64efdb3c0893c80b0defa
Source dataset
uspto-grants-2010_06
Patent number
US07737159B2

Linked notes

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