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Formaldehyde → 4,6-Bis(dimethylaminoethyl)pyrimidine

HRID 1756145
Notes
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Reaction equation

HRID 1756145 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[N:6]=[CH:5][N:4]=1)=[CH2:2].CC1C=[C:16](C)[N:15]=[CH:14]N=1.Cl.[CH3:20][NH:21][CH3:22].C=O>O>[CH3:20][N:21]([CH2:2][CH2:1][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][N:15]([CH3:14])[CH3:16])[N:6]=[CH:5][N:4]=1)[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 152574,6-DimethylpyrimidineHCID 193495094,6-Divinylpyrimidine

Product 1

HCID 542044914,6-Bis(dimethylaminoethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound 4,6-divinylpyrimidine is miscible with water and can be prepared according to the synthetic scheme illustrated in FIG. 1. As shown, in a two-step process, 4,6-dimethylpyrimidine is reacted with dimethylamine hydrochloride and formaldehyde to provide the corresponding 4,6-bis(dimethylaminoethyl)pyrimidine. This dimethylaminoethyl compound is methylated and deaminated in the presence of a base to provide the desired 4,6-divinylpyrimidine.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-aa7cd33d6fbe49b48c4538b4afadb04c
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05439950

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes