Water → (+/-)-[3-[bis(phenylmethyl)amino]-2-hydroxypropyl]-2(1H)pyrimidinone

HRID 983452

Reaction equation

HRID 983452 reaction equation
Cl.[OH:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:15]1([CH2:21][N:22]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH:24]2[CH2:26][O:25]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CO.C1(C)C=CC=CC=1>[C:28]1([CH2:27][N:22]([CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:23][CH:24]([OH:25])[CH2:26][N:4]2[CH:5]=[CH:6][CH:7]=[N:8][C:3]2=[O:2])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11276836N,N-dibenzyl-1-(oxiran-2-yl)methanamineHCID 178479648HCID 178479648, compound

Product 1

HCID 22560818(+/-)-[3-[bis(phenylmethyl)amino]-2-hydroxypropyl]-2(1H)pyrimidinoneYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2-hydroxypyrimidine hydrochloride (1:1) (0.075 mol) in methanol (150 ml) was stirred for 30 minutes and then added to a solution of sodium carbonate (0.075 mol) in methanol (20 ml). The mixture was stirred and refluxed for 15 minutes, and cooled to 55° C. A solution of N,N-bis(phenylmethyl)oxiranmethanamine (0.075 mol) in toluene (160 ml) was added dropwise and the reaction mixture was stirred at 50° C. overnight. Water (75 ml) was added and the mixture was stirred at 55° C. for 15 minutes. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH3OH/CH2Cl2 97/3). The pure fractions were collected and the solvent was evaporated, yielding 11.8 g (45%) of (±)-1-[3-[bis(phenylmethyl)amino]-2-hydroxypropyl]-2(1H)pyrimidinone (interm. 2).

Workup

  1. temperaturerefluxed for 15 minutes
  2. stirringthe reaction mixture was stirred at 50° C. overnight
  3. stirringthe mixture was stirred at 55° C. for 15 minutes
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH3OH/CH2Cl2 97/3)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9eb688e745404af191d496479c6c7af9
Source dataset
uspto-grants-2005_03
Patent number
US06864273B1

Linked notes

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