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

HRID 917289

반응식

HRID 917289 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 1140Toluene용매

반응 조건

온도
55 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5243d7b7f45d49fc819ec067b05b88cf
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273862B2

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