Guanidine → 5-[(1-Methyl-1H-indol-3-yl)methyl]pyrimidine-2,4-diamine

HRID 280704Notes

Reaction equation

HRID 280704 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].Cl.NC(N)=N.C[O-].[Na+].[NH:13]([CH:20]=[C:21]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1)[C:22]#N)C1C=CC=CC=1>C(O)C.COCCO>[NH2:3][C:2]1[N:4]=[C:20]([NH2:13])[C:21]([CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH3:34])[CH:26]=2)=[CH:22][N:1]=1

Participants

7

Reactant 4

HCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 67936950HCID 67936950, compound

Product 1

HCID 130589245-[(1-Methyl-1H-indol-3-yl)methyl]pyrimidine-2,4-diamineYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

To 100 mL of an ethanolic guanidine solution prepared from 2.10 g (0.022 mole) of guanidine hydrochloride and 1.20 g (0.022 mole) of sodium methoxide was added 5.00 g (0.017 mole) of 3-anilino-2-(1-methyl-3-indolylmethyl)acrylonitrile. The solution was heated under reflux for 1/2 hour and then 100 mL of 2-methoxyethanol was added. The internal temperature was allowed to gradually increase to 120° by distillation of the ethanol, after which it was heated at this temperature for 4.75 hr. The reaction was cooled and the solvent was removed in vacuo. The residue was recrystallized from 95% ethanol to give two crops of the title compound (total 1.82 g, 41%) mp 253°-256° dec. Anal. Calcd for C14H15N5 : C, 66.38, H, 5.97; N, 27.65. Found: C, 66.05; H, 6.04; N, 27.89.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 1/2 hour
  3. temperatureafter which it was heated at this temperature for 4.75 hr
  4. temperatureThe reaction was cooled
  5. customthe solvent was removed in vacuo
  6. customThe residue was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-bcb67dcfb54f4a73a7997a4dba39a7f5
Source dataset
uspto-grants-1986_05
Patent number
US04590271

Reaction notes

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