Methyl 4-(3-ethoxymethylene-5,5-dicyanopent-4-en-1-yl)benzoate → HCID 178497708, compound

HRID 330365

Reaction equation

HRID 330365 reaction equation
C(O[CH:4]=[C:5]([CH:18]=C(C#N)C#N)[CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)C.[NH2:24][C:25]1[NH:26][C:27](=[O:32])[CH:28]=[C:29]([NH2:31])[N:30]=1>C(O)(=O)C>[NH2:24][C:25]1[N:26]=[C:27]([OH:32])[C:28]2[CH:4]=[C:5]([CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=3)[CH:18]=[N:31][C:29]=2[N:30]=1

Participants

4

Reactant 2

HCID 53959848Methyl 4-(3-ethoxymethylene-5,5-dicyanopent-4-en-1-yl)benzoateHCID 1354087632-Aminoisocytosine

Product 1

HCID 178497708HCID 178497708, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Two grams of methyl 4-(3-ethoxymethylene-5,5-dicyanopent-4-en-1-yl)benzoate, 0.93 g of 2,4-diamino-6(1H)-pyrimidone, and 30 mL of acetic acid are heated at reflux with stirring for 4 hours. The reaction mixture is allowed to cool to room temperature and the solid which forms is collected by filtration, washed with water and diethyl ether and dried to yield methyl 4-[2-(2-amino-4-hydroxypyrido[2,3-d]pyrimidin6-yl)-ethyl]benzoate, m.p.>300° C.; IR (KBr) νmax 3320, 2950, 1720, 1657, 1626, 1610, 1455, 1280, 1251, 1148, 1109, and 834 cm-1 ; 1H NMR (dTFA, d6DMSO) delta 8.38 (s, 1H (7)--H), 7.99 (s, 1H, (5)--H), 7.55 (d, J=8.0 Hz, 2H, Ar), 6.87 (s, 1H (3)--H), 6.82 (d, J=8.0 Hz, 2H, Ar), 3.56 (s, 3H, --CH3), 2.77-281 (m, 2H, (6)--CH2 --), 2.67-2.73 (m, 2H, benzyl).

Workup

  1. temperatureat reflux
  2. filtrationthe solid which forms is collected by filtration
  3. washwashed with water and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-c4774c67ada5499b8cff8285fcca72c5
Source dataset
uspto-grants-1990_01
Patent number
US04895946

Linked notes

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