Ammonia → 2,6-Dichloro-5-methoxypyrimidin-4-amine

HRID 1912299Notes

Reaction equation

HRID 1912299 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH3:10])=[C:4]([Cl:11])[N:3]=1.[NH3:12].O>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH2:12])[C:5]([O:9][CH3:10])=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 202711362,4,6-Trichloro-5-methoxypyrimidine

Product 1

HCID 591269272,6-Dichloro-5-methoxypyrimidin-4-amineYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2,4,6-Trichloro-5-methoxypyrimidine (1.0 g, 4.7 mmol, see U.S. Pat. No. 3,984,411 for preparation) was dissolved in 15 mL dry dimethyl sulfoxide (DMSO) and treated with a stream of ammonia gas for 30 min. The mixture was poured into 30 mL water and the precipitated product was collected by filtration and washed with water. This solid was dissolved in 40 mL ethyl acetate, washed twice with water, washed once with brine, dried and evaporated to give the title compound (800 mg, 88% yield): mp 155-156° C.: 1H NMR (DMSO-d6+D2O) δ 3.71 (s, 3H).

Workup

  1. custom3,984,411 for preparation)
  2. filtrationthe precipitated product was collected by filtration
  3. washwashed with water
  4. dissolutionThis solid was dissolved in 40 mL ethyl acetate
  5. washwashed twice with water
  6. washwashed once with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-67cea5a8bd6140abbdfcd4cc930e4fc9
Source dataset
uspto-grants-2013_12
Patent number
US08609592B2

Reaction notes

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