Hydrochloric Acid → Ethanone, 1-[4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl]-

HRID 378953

Reaction equation

HRID 378953 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([CH3:19])[N:13]=1.Cl.[OH-].[K+]>O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16]2[CH:15]=[C:14]([CH3:19])[N:13]=[C:12]([NH2:11])[N:17]=2)=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7468p-AminoacetophenoneHCID 14797Potassium HydroxideHCID 218102-Amino-4-chloro-6-methylpyrimidine

Product 1

HCID 353588Ethanone, 1-[4-[(2-amino-6-methyl-4-pyrimidinyl)amino]phenyl]-Yield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound No. 17 (CNI-1794): A suspension of p-aminoacetophenone (1.35 g) and 2-amino-4-chloro-6-methylpyrimidine (1.435 g) in 20 mL water was treated with 0.85 mL conc HCl and heated at reflux for 1 hr. Addition of 20 mL 1N KOH gave a light buff solid, which was filtered out and dried to give 2.28 g 4-(4-acetylphenyl)amino-2-amino-6-methylpyrimidine, mp 194-196° C. Of this, 1.21 g was treated with methyl iodide (3 mL) in dimethylformamide (15 mL) at room temperature for 42 hr. Dilution with ethyl acetate and filtration gave 1.11 g 4-(4-acetylphenyl)amino-2-amino-1,6-dimethylpyrimidinium iodide as a white powder, mp 302-3° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. customgave a light buff solid, which
  4. filtrationwas filtered out
  5. customdried

Sources & evidence

ORD record
ord-593d94b20bdc46398cfdb4d5e384faf8
Source dataset
uspto-grants-2001_10
Patent number
US06297253B1

Linked notes

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