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

HRID 2211449Notes

Reaction equation

[CH2:1]([C:3]1[NH:4][C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=1)[CH3:2].Br[CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.[H-].[Na+]>>[CH2:1]([C:3]1[N:4]([CH2:12][CH2:13][O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=1)[CH3:2]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 2627064-(2-Bromoethoxy)Benzaldehyde

HCID 1354173682-Ethyl-6-methylpyrimidin-4(1h)-one

Product 1

HCID 117481474-[2-[2-Ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehydeYield 42%

Procedure

The title compound (1.7 g, 42%) was prepared from 2-ethyl-4-methyl-1,6-dihydro-6-pyrimidone (2.0 g, 14.49 mmol), 4-[2-bromoethoxy]benzaldehyde (332 g, 14.19 mmol). LIBr (2.9 g, 33.33 mmol) and NaH (0.45 g, 18.84 mmol) as base, by a similar procedure to that described in preparation 1.

Sources & evidence

ORD record: ord-0a99f9f82b7e47b9a5a2b51cc9c7ed24
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039266E1

Reaction notes

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