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

HRID 983453Notes

Reaction equation

HRID 983453 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:14]1([CH2:20][N:21]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH:23]2[CH2:25][O:24]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CO.C1(C)C=CC=CC=1>[C:27]1([CH2:26][N:21]([CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:22][CH:23]([OH:24])[CH2:25][N:3]2[CH:4]=[CH:5][CH:6]=[N:7][C:2]2=[O:1])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11276836N,N-dibenzyl-1-(oxiran-2-yl)methanamineHCID 178517760HCID 178517760, compound

Product 1

HCID 22560818(+/-)-[3-[bis(phenylmethyl)amino]-2-hydroxypropyl]-2(1H)pyrimidinoneYield 47.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2-hydroxypyrimidine (0.16 mol) in methanol (300 ml) was stirred at room temperature for 30 minutes. A solution of Na2CO3 (0.16 mol) in methanol (40 ml) was added. The mixture was stirred and refluxed for 15 minutes and cooled to 55° C. A solution of N,N-bis(phenylmethyl)-2-oxiranemethanamine (0.16 mol) in toluene (320 ml) was added dropwise. The mixture was stirred at 50° C. overnight Water (150 ml) was added 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: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 26.55 g of (±)-[3-[bis(phenylmethyl)amino]-2-hydroxypropyl]-2(1H)pyrimidinone (intermediate 4).

Workup

  1. temperaturerefluxed for 15 minutes
  2. additionwas added The mixture
  3. stirringwas 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: CH2Cl2/CH3OH 97/3)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8f1dcbd0ae55455dac3920140bf482d1
Source dataset
uspto-grants-2005_03
Patent number
US06864273B1

Reaction notes

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