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

HRID 917289

反応式

HRID 917289 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5243d7b7f45d49fc819ec067b05b88cf
出典データセット
uspto-grants-2007_09
特許番号
US07273862B2

関連ノート

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