Water → N-Methyl-9-vinyl-9H-purin-6-amine

HRID 2041905Notes

Reaction equation

HRID 2041905 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]=[CH2:12].[CH3:13][NH2:14].O.Cl.CN>C1COCC1>[CH3:13][NH:14][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]=[CH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 6364545Methylamine hydrochlorideHCID 109541366-Chloro-9-vinyl-9H-purine

Product 1

HCID 23649897N-Methyl-9-vinyl-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-9-vinylpurine (JOC 1968, 33, 1341) (0.54 g, 3 mmol), was added to methylamine (˜15 mmol, 2.0M in THF) in THF (5 mL) and the mixture was stirred for 5 h at rt. Water was added to dissolve the white precipitate (methylamine hydrochloride). The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, concentrated on a rotavap, and then subjected to silica gel column chromatography (5% methanol/methylene chloride) yielding the desired product.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated on a rotavap

Sources & evidence

ORD record
ord-4900766008484c3097bf3fce12f42405
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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