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

HRID 247078

Reaktionsgleichung

Reaktionsgleichung von HRID 247078
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4befa2d04d2f46b59660f0ff4ad4ab2c
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705791

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