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

HRID 247078

Reaction equation

HRID 247078 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4befa2d04d2f46b59660f0ff4ad4ab2c
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Linked notes

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