Triethylamine → 5-Chloro-1-[(4-methylphenoxy)methyl]pyrimidin-2(1H)-one

HRID 247070Notes

Reaction equation

HRID 247070 reaction equation
Cl[CH2:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.Cl.[Cl:12][C:13]1[CH:14]=[N:15][C:16](=[O:19])[NH:17][CH:18]=1.C(N(CC)CC)C.[K+].[Br-]>ClCCl.CCOCC.CC(C)=O>[C:7]1([CH3:10])[CH:8]=[CH:9][C:4]([O:3][CH2:2][N:17]2[CH:18]=[C:13]([Cl:12])[CH:14]=[N:15][C:16]2=[O:19])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 253877Potassium BromideHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 130629301-(Chloromethoxy)-4-methylbenzene

Product 1

HCID 130629355-Chloro-1-[(4-methylphenoxy)methyl]pyrimidin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared by adding a solution of 4-(chloromethoxy)toluene (see J.Appl. Chem. 3, 266(1953)) (10 mmol) in dichloromethane (10 ml) to a solution of 5-chloropyrimidin-2-one hydrochloride (10 mmol) and triethylamine (20 mmol) in dichloromethane (50 ml). The mixture was stirred at room temperature for 2 days. The product, 1.90 g (76%), consisted of the N- and O-isomers in the ratio 3:1. The N-isomer was isolated by its lower solubility in ether; m.p. 186° C. (acetone). (Found: C57.59; H4.65 Calc. for C12H11ClN2O2 : C57.49; H4.43) 1H NMR (CDCl3): δ 2.25 (Me), 5.74 (CH2), 6.8-7.3 (Ph), 7.80 and 8.50 (H-4 and H-6, respectively, J 3 Hz). IR (KBr): 1680 cm-1 (CO). MS [70 eV, m/z% rel. int.)[: 250 (7,M), 145 (31), 143 (100), 116 (28).

Sources & evidence

ORD record
ord-8557c1331103476eb4ff08efb62b90bc
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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