3-benzyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbaldehyde → 3-benzyl-2-(1-hydroxy-2-methylprop-2-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1784465Notes

Reaction equation

[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]2=[N:10][C:9]=1[CH:19]=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([Mg]Br)([CH3:23])=[CH2:22]>C1COCC1>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]2=[N:10][C:9]=1[CH:19]([OH:20])[C:21]([CH3:23])=[CH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 500 mg (1.9 mmol) of the product from Step 6 (16) in 15 ml THF was cooled to −78° C. To the resulting solution was added dropwise 7.6 ml (3.8 mmol) of isopropenylmagnesium bromide and stirred at −78° C. for 2 hours. The reaction was quenched with saturated NH4Cl and extracted with ethyl acetate (2×). The combined organic layers were dried over MgSO4 and the solvent was removed in vacuo yielding 613 mg (2.0 mmol, 106%) of 3-benzyl-2-(1-hydroxy-2-methylprop-2-enyl)-4H-pyrido [1,2-a]pyrimidin-4-one (17) as a pale yellow solid. This was purified by flash chromatography.

Workup

customThe reaction was quenched with saturated NH4Cl
extractionextracted with ethyl acetate (2×)
dry with materialThe combined organic layers were dried over MgSO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-5b3825057f854ccab44104ace7905bbb
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504405B2

Reaction notes

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