Triethylamine → 5-Chloro-1-(phenoxymethyl)pyrimidin-2(1H)-one

HRID 1982554

반응식

HRID 1982554 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.C(N(CC)CC)C.Cl[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[O:18]([CH2:17][N:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[N:6][C:5]1=[O:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 81201(Chloromethoxy)benzeneHCID 1085785-Chloro-2(1H)-pyrimidinone

생성물 1

HCID 130629345-Chloro-1-(phenoxymethyl)pyrimidin-2(1H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

5-Chloropyrimidin-2-one (5 mmol) and triethylamine (5 mmol) were stirred together in dichloromethane (50 ml). When all the solid had dissolved a solution of chloromethoxybenzene (see Preparation 2) (5 mmol) in dichloromethane (25 ml) was added with stirring at room temperature. The resultant mixture was stirred for 24 h at this temperature before the solvent was distilled off. The residue was triturated with water (30 ml), extracted into chloroform (3×20 ml), and the dried (MgSO4) solution evaporated to yield a mixture of the title compound and the O-alkylated isomer in the ratio 3:1; yield 7.00 g (85%). The N-isomer was separated by column chromatography on silica gel; m.p. 146° C. 1H NMR (CDCl3): δ 5.92 (CH2), 6.8-7.4 (Ph), 7.80 and 8.43 (H-4 and H-6, respectively, J 3 Hz). IR (KBr): 1660 cm-1 (CO). MS (70 eV, m/z (% rel. int.)): 236 (7, M), 145 (32), 143 (100), 116 (31), 94 (6), 77 (18).

후처리

  1. additionwas added
  2. distillationwas distilled off
  3. customThe residue was triturated with water (30 ml)
  4. extractionextracted into chloroform (3×20 ml)
  5. dry with materialthe dried (MgSO4) solution
  6. customevaporated
  7. customto yield

출처 및 근거

ORD 기록
ord-fce50a9b3e6a427eb173337aa08412c8
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04596870

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