HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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 1784465
Notes
Print preview

Reaction equation

HRID 1784465 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 596541753-benzyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbaldehydeHCID 178456138HCID 178456138, compound

Product 1

HCID 575932043-benzyl-2-(1-hydroxy-2-methylprop-2-enyl)-4H-pyrido[1,2-a]pyrimidin-4-oneYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes