Triethylamine → 1-(Phenoxy)methyl-4,6-dimethyl-5-bromopyrimidin-2-one

HRID 1982565ノート

反応式

HRID 1982565 の反応式
[CH3:1][C:2]1[C:7]([Br:8])=[C:6]([CH3:9])[NH:5][C:4](=[O:10])[N:3]=1.C(N(CC)CC)C.Cl[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[O:20]([CH2:19][N:3]1[C:2]([CH3:1])=[C:7]([Br:8])[C:6]([CH3:9])=[N:5][C:4]1=[O:10])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 81201(Chloromethoxy)benzeneHCID 6088115-Bromo-4,6-dimethylpyrimidin-2-ol

生成物 1

HCID 201613411-(Phenoxy)methyl-4,6-dimethyl-5-bromopyrimidin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
40 °C

実験手順

A mixture of 4,6-dimethyl-5-bromopyrimidin-2-one (4.7 mmol) and triethylamine (4.7 mmol) in dichloromethane (60 ml) was heated at 40° C. for dissolution. The solution was then cooled to room temperature and (chloromethoxy)benzene [see Preparation 2] (4.7 mmol) in dichloromethane (15 ml) was added. The resultant mixture was stirred at room temperature for 11/2 h, the solvent distilled off, the mixture triturated with water, the remaining solid extracted with chloroform, the dried (MgSO4) chloroform solution evaporated, the residue triturated with a little ether, the residue redissolved in chloroform and the solution chromatographed on a column of alumina, activity III, using chloroform, Yield 0,35 g (24%), m.p. 120° C. (CCl4) (Found C50.32; H4.15. Calc. for C13H13BrN2O2 : C50.50; H4.25) 1H NMR (CDCl3): δ 2.50 and 2.68 (4-Me and 6-Me), 6.03 (CH2), 6.8-7.4 (Ph), MS [70 eV, m/z (% rel. int)]. 310/308 (6/7,M), 217(97), 215(100), 174(15), 172(12), 136(20), 135(19), 108(23) 94(19).

後処理

  1. temperatureThe solution was then cooled to room temperature
  2. distillationthe solvent distilled off
  3. customthe mixture triturated with water
  4. extractionthe remaining solid extracted with chloroform
  5. dry with materialthe dried (MgSO4) chloroform solution
  6. customevaporated
  7. customthe residue triturated with a little ether
  8. dissolutionthe residue redissolved in chloroform
  9. customthe solution chromatographed on a column of alumina, activity III

出典と根拠

ORDレコード
ord-42c06a1cb4ea40f28e4d902995e79420
出典データセット
uspto-grants-1986_06
特許番号
US04596870

反応ノート

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