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

HRID 1982554

反応式

HRID 1982554 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fce50a9b3e6a427eb173337aa08412c8
出典データセット
uspto-grants-1986_06
特許番号
US04596870

関連ノート

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