Hydrochloric Acid → 2,5-Dimethoxy-4-cyanoaminopyrimidine

HRID 1467375Notes

Reaction equation

HRID 1467375 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([O:10][CH3:11])[N:3]=1.[N:12]#[C:13][NH2:14].[Na].O.Cl>CN1CCCC1=O>[CH3:11][O:10][C:4]1[N:3]=[C:2]([NH:14][C:13]#[N:12])[C:7]([O:8][CH3:9])=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 99422744-Chloro-2,5-dimethoxypyrimidineHCID 57375518Cyanamidnatrium

Product 1

HCID 867130532,5-Dimethoxy-4-cyanoaminopyrimidineYield 76.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

4-Chloro-2,5-dimethoxypyrimidine (CDMP; 15 g, 0.086 mol) was dissolved in N-methyl-2-pyrrolidinone (NMP; 62.5 g) at ambient temperature. Sodium hydrogen cyanamide (12.1 g, 2.2 eq) was added all at once, and the mixture was heated to 50° C. with stirring for 2.5 h. The resulting slurry was cooled to 25° C., and 150 mL of water was added. Concentrated hydrochloric acid was added drop-wise until a pH of 5.5 was reached. The thick slurry was filtered and washed twice with 10 mL of water to afford 2,5-dimethoxy-4-cyanoamino-pyrimidine (2) as a white solid (11.83 g, 76% yield).

Workup

  1. temperatureThe resulting slurry was cooled to 25° C.
  2. filtrationThe thick slurry was filtered
  3. washwashed twice with 10 mL of water

Sources & evidence

ORD record
ord-c4f614feb1174568924ce917ff57e568
Source dataset
uspto-grants-2015_04
Patent number
US09000160B2

Reaction notes

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