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

HRID 655795Notes

Reaction equation

HRID 655795 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].[CH:13]1([NH2:16])[CH2:15][CH2:14]1.O.Cl.C1(N)CC1>C1COCC1>[CH:13]1([NH:16][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:11]=[CH2:12])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 69828CyclopropylamineHCID 109541366-Chloro-9-vinyl-9H-purineHCID 11708049Cyclopropylamine hydrochloride

Product 1

HCID 68923757N-cyclopropyl-9-vinyl-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-9-vinylpurine (0.54 g, 3 mmol) was mixed with cyclopropylamine (1.71 g, 30 mmol) in THF (10 mL) and the mixture was stirred for 5 h at rt. Water was added to dissolve the white precipitate (cyclopropylamine 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 recrystallized from EtOAc/hexanes 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
  4. customrecrystallized from EtOAc/hexanes yielding the desired product

Sources & evidence

ORD record
ord-31be81757d0f4529a567a8b72ab35db0
Source dataset
uspto-grants-2011_12
Patent number
US08071609B2

Reaction notes

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