Guanidine → Diaveridine
Reaction equation
C(O)(=O)C1C=CC(OC)=C(OC)C=1.COC1C=C(C=CC=1OC)C(OC)=O.[BH4-].[Na+].CS(CC(O)C1C=CC(OC)=C(OC)C=1)=O.N(CCC#N)C1C=CC=CC=1.C[O-].[Na+].[CH3:60][O:61][C:62]1[CH:63]=[C:64]([CH:77]=[CH:78][C:79]=1[O:80][CH3:81])[CH2:65][C:66](=[CH:69]NC1C=CC=CC=1)[C:67]#[N:68].[NH2:82][C:83]([NH2:85])=[NH:84]>CO.Cl.CN(C)P(N(C)C)(N(C)C)=O>[NH2:84][C:83]1[N:85]=[C:67]([NH2:68])[C:66]([CH2:65][C:64]2[CH:77]=[CH:78][C:79]([O:80][CH3:81])=[C:62]([O:61][CH3:60])[CH:63]=2)=[CH:69][N:82]=1Participants
12
Reactant 8
HCID 3520Guanidine
HCID 7121Veratric Acid
HCID 141003-Anilinopropionitrile
HCID 16522Methyl 3,4-Dimethoxybenzoate
HCID 121619alpha-(3,4-Dimethoxybenzyl)-beta-anilinoacrylonitrile
HCID 4311764Sodium borohydride
HCID 10942334Sodium Methoxide
HCID 21498650beta-Hydroxy-beta-(3,4-dimethoxyphenyl)ethyl methyl sulphoxideProduct 1
Reagents, catalysts & solvents 3
Procedure
Veratric acid is esterified by refluxing in methanol using hydrochloric acid as catalyst. The resulting methyl 3,4-dimethoxybenzoate is converted under the conditions of Example 103 to ω-(methylsulfinyl) 3,4-dimethoxyacetophenone. This is reduced with sodium borohydride under the condition of Example 104 to β-hydroxy-β-(3,4-dimethoxyphenyl)ethyl methyl sulphoxide, which is then allowed to react with β-anilinopropionitrile in hexamethylphosphoramide containing sodium methylate according to Example 105. The resulting α-(3,4-dimethoxybenzyl)-β-anilinoacrylonitrile is condensed with guanidine according to Example 106 to give 2,4-diamino-5-(3',4'-dimethoxybenzyl) pyrimidine, m.p. 224°-229° C.
Sources & evidence
- ORD record
- ord-af6dbb4eb1304876bcebf8517cef0143
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03991050
Reaction notes
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