Guanidine → 2,4-Diamino-5-(4-methoxy-1-naphthylmethyl)pyrimidine hydrochloride

HRID 746207Notes

Reaction equation

HRID 746207 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].[ClH:5].NC(N)=N.C[O-].[Na+].[NH:13]([CH:20]=[C:21]([CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([O:35][CH3:36])=[CH:27][CH:26]=1)[C:22]#N)C1C=CC=CC=1>C(O)C.COCCO>[ClH:5].[NH2:3][C:2]1[N:4]=[C:20]([NH2:13])[C:21]([CH2:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([O:35][CH3:36])=[CH:27][CH:26]=2)=[CH:22][N:1]=1

Participants

7

Reactant 4

HCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 704518803-Anilino-2-(4-methoxy--naphthylmethyl)acrylonitrile

Product 1

HCID 233106042,4-Diamino-5-(4-methoxy-1-naphthylmethyl)pyrimidine hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

To 65 mL of ethanolic guanidine solution prepared from 3.42 g (35.8 mmol) of guanidine hydrochloride and 2.00 g (37.0 mmol) of sodium methoxide was added 9.00 g (28.6 mmol) of 3-anilino-2-(4-methoxy--naphthylmethyl)acrylonitrile. The solution was heated under reflux for 1.5 hr, and then 60 mL of 2-methoxyethanol was added. The internal temperature was allowed to gradually increase to 108° by distillation of the ethanol, after which it was heated at this temperature for 2.5 hr. The hot mixture was filtered, and the precipitate (7.04 g, 87% of crude product) recrystallized from 30% ethanol in the presence of hydrochloric acid, to give the title compound; mp 312°-314° dec. Anal. Calcd for C16H16N4O.HCl: C, 60.66; H, 5.41; N, 17.69; Cl, 11.19. Found: C, 60.67; H, 5.45; N, 17.70; Cl, 11.19.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 1.5 hr
  3. temperatureafter which it was heated at this temperature for 2.5 hr
  4. filtrationThe hot mixture was filtered
  5. customthe precipitate (7.04 g, 87% of crude product) recrystallized from 30% ethanol in the presence of hydrochloric acid

Sources & evidence

ORD record
ord-f854131d278f46aa9dbdb679d8feefbb
Source dataset
uspto-grants-1986_07
Patent number
US04603136

Reaction notes

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