Dimethylamine → 2-Dimethylamino-4-sec. butylamino-5-nitro-6-methylpyrimidine

HRID 597468Notes

Reaction equation

HRID 597468 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:11][CH3:12])[CH3:10])[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:16])[N:3]=1.[CH3:17][NH:18][CH3:19]>C(N(CC)CC)C>[CH3:17][N:18]([CH3:19])[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:11][CH3:12])[CH3:10])[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 18801449HCID 18801449, compound

Product 1

HCID 1317106992-Dimethylamino-4-sec. butylamino-5-nitro-6-methylpyrimidineYield 98.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

10 ml of triethylamine are added to a solution of 15.9 g of 2-chloro-4-sec. butylamino-5-nitro-6-methylpyrimidine (0.065 mole) in 250 ml of alcohol. Then 4.5 g (0.1 mole) of dimethylamine are passed in and the mixture is boiled for 4 hours at 100° C. After it has cooled, the mixture is evaporated and the residue is suspended in water. The resultant precipitate is filtered off with suction and washed with water until no more chlorine ions are dissolved out. The product is dried in a water jet vacuum at 50° C to yield 16.2 g of 2-dimethylamino-4-sec. butylamino-5-nitro-6-methylpyrimidine (=98.5% yield) of m.p. 98°-100° C. On recrystallisation from petroleum ether, the melting point of the product rises to 109°-110° C.

Workup

  1. temperatureAfter it has cooled
  2. customthe mixture is evaporated
  3. filtrationThe resultant precipitate is filtered off with suction
  4. washwashed with water until no more chlorine ions
  5. dissolutionare dissolved out
  6. dry with materialThe product is dried in a water jet vacuum at 50° C

Sources & evidence

ORD record
ord-ee187218e1834252a4c18fd108ecbe5e
Source dataset
uspto-grants-1977_03
Patent number
US04014677

Reaction notes

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