Triethylamine → HCID 20267952, compound

HRID 1719250Notes

Reaction equation

HRID 1719250 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][O:14][CH2:15]Cl)=[CH:11][CH:10]=1.[Cl:19][C:20]1[CH:21]=[N:22][C:23](=[O:26])[NH:24][CH:25]=1.C(N(CC)CC)C>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][O:14][CH2:15][N:24]2[CH:25]=[C:20]([Cl:19])[CH:21]=[N:22][C:23]2=[O:26])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 202679362-({4-[(Chloromethoxy)methyl]phenyl}methoxy)oxane

Product 1

HCID 20267952HCID 20267952, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloromethyl 4-(tetrahydropyran-2-yloxymethyl)benzyl ether (see Preparation 12) (4.7 mmol) in dichloromethane (40 ml) was added dropwise with stirring to a solution of 5-chloropyrimidin-2-one (4.7 mmol) and triethylamine (4.7 mmol) in dichloromethane (10 ml). The mixture was stirred at room temperature for 2 hours and was then washed with water, the organic solution dried (MgSO4) and the solvent distilled off to yield a crude product in 89% yield (1.53 g), which was extracted with ether and the residual material purified on neutral alumina eluting with dichloromethane and subsequently with 10% MeOH in dichloromethane; yield 0.42 g (26%) of the non-crystalline title compound. 1H NMR (CDCl3): δ1.4-2.0 (6H, m, THP), 3.3-4.3 (2H, m), 4.5-4.9 (2CH2, CH), 5.37 (NCH2), 7.38 (Ph), 7.88 and 8.53 (H-4, H-6, J 4 Hz).

Workup

  1. washwas then washed with water
  2. dry with materialthe organic solution dried (MgSO4)
  3. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-cefdc0c30c294e1692ebd1e07588eb4d
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

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