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

HRID 247078

반응식

HRID 247078 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4befa2d04d2f46b59660f0ff4ad4ab2c
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04705791

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