Hydrochloric Acid → 6-Methyl-2,4-pyrimidinediamine

HRID 1899827Notes

Reaction equation

HRID 1899827 reaction equation
[NH2:1]C1C=CC(C(=O)C)=CC=1.[NH2:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([CH3:19])[N:13]=1.Cl.[OH-].[K+]>O>[NH2:1][C:16]1[CH:15]=[C:14]([CH3:19])[N:13]=[C:12]([NH2:11])[N:17]=1

Participants

6

Reactant 4

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

Product 1

HCID 2297436-Methyl-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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 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-7a69ce225bca45c7ae846e181ff9f5d5
Source dataset
uspto-grants-1996_11
Patent number
US05574040

Reaction notes

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