Pyrimidine → HCID 13067041, compound

HRID 1759196Notes

Reaction equation

HRID 1759196 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:4][N:3]=1.[CH2:13]([NH2:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH-].[NH4+].N1C=CC=NC=1>C(Cl)Cl.CO.C(Cl)(Cl)Cl.O.C(O)C>[CH2:13]([NH:25][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:4][N:3]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

10

Reactant 4

HCID 9260PyrimidineHCID 13583DodecylamineHCID 14923Ammonium HydroxideHCID 13067039HCID 13067039, compound

Product 1

HCID 13067041HCID 13067041, compoundYield 84.4%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-4-(3-hydroxypropylamino)pyrimidine (37 g, 0.2 m), n-dodecylamine (81.5 g, 0.44 m), ethanol (2.5 l) and water (250 ml) is heated under reflux until thin layer chromatography (silica gel; 7.5 parts by volume chloroform, 0.5 parts by volume concentrated ammonium hydroxide, and 2.0 parts by volume methanol) indicates absence of the pyrimidine starting material. After concentration of the mixture, the residue is taken up in methylene chloride, and filtered from some n-dodecylamine hydrochloride. The organic solution is washed with water, dried and concentrated, and the residue is chromatographed on silica gel using a chloroform-ethanol eluant system (0-10% by volume of ethanol) to yield 56 g of 2-n-dodecylamino-4-(3-hydroxypropylamino)pyrimidine, m.p. 58°-59° C.

Workup

  1. temperatureis heated
  2. filtrationfiltered from some n-dodecylamine hydrochloride
  3. washThe organic solution is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue is chromatographed on silica gel using a chloroform-ethanol eluant system (0-10% by volume of ethanol)

Sources & evidence

ORD record
ord-287d788594364feaaeb1cc7ccb308223
Source dataset
uspto-grants-1982_07
Patent number
US04339453

Reaction notes

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