Sodium hydride → 4-[2-[2-Ethyl-4-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde

HRID 841989Notes

Reaction equation

HRID 841989 reaction equation
[CH2:1]([C:3]1[NH:4][C:5](=[O:15])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:2].Br[CH2:17][CH2:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.[Li+].[Br-].[H-].[Na+]>>[CH2:1]([C:3]1[N:4]([CH2:17][CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)[C:5](=[O:15])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:2]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 2627064-(2-Bromoethoxy)BenzaldehydeHCID 1354734072-Ethyl-6-phenyl-4(3H)-pyrimidinone

Product 1

HCID 219601434-[2-[2-Ethyl-4-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehydeYield 44.2%

Procedure

The title compound (2.0 g, 44%) was prepared from 2-ethyl-4-phenyl-1,6-dihydro-6-pyrimidone (2.6 g, 13.0 mmol), 4-[2-bromoethoxy]benzaldehyde (2.97 g, 13.0 mmol) and LiBr (2.59 g, 29.9 mmol) in the presence of NaH as base (0.4 g, 16.9 mmol) by a similar procedure to that described in preparation 1.

Workup

  1. customthat described in preparation 1

Sources & evidence

ORD record
ord-dd5baf51167d43cbbdd14fcb5912bc71
Source dataset
uspto-grants-2002_04
Patent number
US06372750B2

Reaction notes

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