Pyrimidine → HCID 20532447, compound

HRID 1759197Notes

Reaction equation

HRID 1759197 reaction equation
[CH2:1]([NH:13][C:14]1[N:19]=[C:18]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:17]=[CH:16][N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br:25][CH2:26][CH2:27][CH2:28][OH:29].[OH-].[NH4+].N1C=CC=NC=1>CN(C)C=O.CCOCC.CO.C(Cl)(Cl)Cl>[Br-:25].[CH2:1]([NH:13][C:14]1[N:19]=[C:18]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:17]=[CH:16][N+:15]=1[CH2:26][CH2:27][CH2:28][OH:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

9

Reactant 4

HCID 9260PyrimidineHCID 123083-Bromo-1-propanolHCID 14923Ammonium HydroxideHCID 13067041HCID 13067041, compound

Product 1

HCID 20532447HCID 20532447, compoundYield 68.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(n-dodecylamino)-4-(3-hydroxypropylamino)pyrimidine (0.67 g, 0.002 m) in dried dimethylformamide (10 ml) is treated with 3-bromo-1-propanol (0.31 g, 0.0022 m) and the resultant mixture is stirred at 35° C. 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 the absence of starting pyrimidine. After cooling to room temperature, ether (50 ml) is added slowly to the mixture, the mixture is allowed to stir for 0.5 hour, the supernatant is decanted from the oil that separates, the oil is stirred vigorously with three separate portions of fresh ether, and then pumped dry to yield 0.65 g of 2-(n-dodecylamino)-1-(3-hydroxypropyl)-4-(3-hydroxypropylamino)pyrimidinium bromide as an oil.

Workup

  1. customthe supernatant is decanted from the oil that separates
  2. stirringthe oil is stirred vigorously with three
  3. customseparate portions of fresh ether
  4. custompumped dry

Sources & evidence

ORD record
ord-f123c602e28445d18dc5791662bd308a
Source dataset
uspto-grants-1982_07
Patent number
US04339453

Reaction notes

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