Triethylamine → 5-Chloro-1-{[(naphthalen-2-yl)oxy]methyl}pyrimidin-2(1H)-one

HRID 1982571Notes

Reaction equation

HRID 1982571 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.C(N(CC)CC)C.Cl[CH2:18][O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1>C(Cl)Cl>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[O:19][CH2:18][N:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]1=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 130629312-(Chloromethoxy)naphthalene

Product 1

HCID 130629395-Chloro-1-{[(naphthalen-2-yl)oxy]methyl}pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Chloropyrimidine-2-one hydrochloride (5 mmol) and triethylamine were stirred together in CH2Cl2 (30 ml). When all the solid had dissolved there was added a solution of 2-chloromethoxynaphthalene [see Preparation 13] (5 mmol) in CH2Cl2 (10 ml) with stirring at room temperature for 5 minutes. The mixture was stirred at room temperature for 24 hours before the solvent was distilled off. The residue was triturated with water, extracted into CHCl3, dried (MgSO4) and evaporated to give a mixture of the tite compound and the O-alkylated isomer in the ratio 4:1. Yield 1.27 g (86%). The O-isomer was removed from the product by extraction with ether followed by recrystallization of the N-isomer from acetone m.p. 168° C. 1H NMR (CDCl3 δ): 5.85 (s, CH2), 7.10-8.1 (m, 8H. Ar+H-4), 8.48 (H-6, d7 =4 Hz) IR (KBr, cm -1): 1675 (CO).

Workup

  1. dissolutionWhen all the solid had dissolved there
  2. stirringThe mixture was stirred at room temperature for 24 hours before the solvent
  3. distillationwas distilled off
  4. customThe residue was triturated with water
  5. extractionextracted into CHCl3
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give
  9. additiona mixture of the tite compound
  10. customThe O-isomer was removed from the product by extraction with ether
  11. customfollowed by recrystallization of the N-isomer from acetone m.p. 168° C

Sources & evidence

ORD record
ord-f21c2a6663504a78957f894565dad85d
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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