Methylamine → 6-ethyl-5-[4-(methylamino)-3-nitrophenyl]pyrimidine-2,4-diamine

HRID 981515Notes

Reaction equation

HRID 981515 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)=[C:4]([CH2:19][CH3:20])[N:3]=1.[CH3:21][NH2:22]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:22][CH3:21])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)=[C:4]([CH2:19][CH3:20])[N:3]=1

Participants

3

Reactant 2

HCID 6329Methylamine2×HCID 3274042,4-Diamino-5-(3-amino-4-chloro-5-nitrophenyl)-6-ethylpyrimidine

Product 1

HCID 46020076-ethyl-5-[4-(methylamino)-3-nitrophenyl]pyrimidine-2,4-diamineYield 92%

Procedure

A suspension of 2,4-Diamino-5-(4-chloro-3-nitro phenyl)-6-ethylpyrimidine (nitropyrimethamine) (10 g) in aqueous methylamine solution (40%; 200 ml) was refluxed for 48 hours with the further addition of methylamine solution (100 ml) after 24 hours and 36 hours. An orange colour slowly developed and the consumption of starting material was monitored by t.l.c. After cooling and dilution with water, the crystalline product was collected and recrystallized from aqueous DMF to yield orange prisms of 2,4-Diamino-5-(4-methylamino-3-nitrophenyl)-6-ethylpyrimidine (9.0 g. 92%), m.p. 262°-265° C. (Elemental analysis: C, 53.9; H, 5.9; N, 29.3%; calculated: C, 54.2; H, 5.6; N, 29.2%).

Workup

  1. customthe consumption of starting material
  2. temperatureAfter cooling
  3. customdilution with water, the crystalline product was collected
  4. customrecrystallized from aqueous DMF

Sources & evidence

ORD record
ord-99a8eae1189643218e5c5dfb1f8beba6
Source dataset
uspto-grants-1991_02
Patent number
US04992444

Reaction notes

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