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-hydroxyprop-2-enyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1784474
Notes
Print preview

Reaction equation

HRID 1784474 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.[CH:21]([Mg]Br)=[CH2:22]>C1COCC1>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]2=[N:10][C:9]=1[CH:19]([OH:20])[CH:21]=[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 178418507HCID 178418507, compound

Product 1

HCID 689099443-benzyl-2-(1-hydroxyprop-2-enyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-oneYield 104.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 2.5 g (9.5 mmol) of the product from Step 6 (16) in 35 mL THF was cooled to −78° C. To the resulting solution was added dropwise 11.4 mL (11.4 mmol) of vinyl magnesium bromide and stirred at −78° C. for 3 hours. The reaction was quenched with saturated NH4Cl and extracted with ethyl acetate (4×). The combined organic layers were dried over MgSO4 and the solvent was removed in vacuo yielding 2.95 g of 3-benzyl-2-(1-hydroxyprop-2-enyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (23) as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-c8395e7f2660426fb4fea0f25dd79e4e
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07504405B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes