Hydrochloric Acid → 5-[(4-Amino-3-methoxyphenyl)methyl]pyrimidine-2,4-diamine

HRID 279983

Reaction equation

HRID 279983 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9]O)=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[C:14]([NH2:19])=[CH:15][CH:16]=[CH:17][CH:18]=1.Cl>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:17]2[CH:16]=[CH:15][C:14]([NH2:19])=[C:13]([O:12][CH3:11])[CH:18]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70002-MethoxyanilineHCID 2958782,4-Diamino-5-pyrimidinemethanol

Product 1

HCID 130431285-[(4-Amino-3-methoxyphenyl)methyl]pyrimidine-2,4-diamineYield 70.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6.30 g (0.045 mol) of 2,4-diamino-5-hydroxymethylpyrimidine, 6.15 g (0.05 mol) of o-anisidine and 3.75 ml of concentrated hydrochloric acid in 55 ml of glacial acetic acid was heated to reflux for 6 hours. The mixture was stirred at room temperature overnight. The solvent was removed under vaccum and the residue was taken up in water, made basic with ammonium hydroxide, and the aqueous solution was extracted with dichloromethane:methanol/3:1. The organic layers were combined, dried and concentrated to a purple glass. This was purified on a silica gel column to give 7.81 g of the 4-N-acetylated product.

Workup

  1. temperatureto reflux for 6 hours
  2. customThe solvent was removed under vaccum
  3. extractionthe aqueous solution was extracted with dichloromethane
  4. customdried
  5. concentrationconcentrated to a purple glass
  6. customThis was purified on a silica gel column

Sources & evidence

ORD record
ord-9654bf1c191345a1808a8d4d149be06c
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Linked notes

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