Benzaldehyde → Phenyl methoxymethyl cinnamonitrile

HRID 1677232Notes

Reaction equation

HRID 1677232 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:12])[CH:10]=[CH2:11].[CH3:13][O-:14].[Na+]>>[C:2]1([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH2:11][O:14][CH3:13])[C:9]#[N:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 7855AcrylonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 67053415Phenyl methoxymethyl cinnamonitrile

Procedure

In the procedure of Scheme C, benzaldehyde a is treated with acrylonitrile in the presence of sodium methoxide in step 1 to afford a phenyl methoxymethyl cinnamonitrile compound q, which in turn is reacted with guanidine in step 2 to yield the diaminopyrimidine r. Diamino pyrimidine r is a compound of formula (I) in which X is —CH2—, Y is —NH2 and R6, R7 and R8 are hydrogen.

Sources & evidence

ORD record
ord-ce04cf5670eb4e3cb6eb712de88eee5f
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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