Water → 4-(2-chloro-9H-purin-6-yl)morpholine

HRID 876514Notes

Reaction equation

HRID 876514 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4](Cl)[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 32746034-(2-chloro-9H-purin-6-yl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dichloro-9H-purine (1.2 g, 6.35 mmol) in N,N-dimethylformamide (5 mL) was added morpholine (553 mg, 6.35 mmol) followed by diisopropylethyl amine (1.2 mL, 6.87 mmol), dropwise via a syringe. The solution was stirred at room temperature for 1 hour until precipitate formed. The reaction mixture was then poured into water and the precipitate was filtered. Upon drying under high vacuum, 2-chloro-6-morpholin-4-yl-9H-purine was isolated as an off-white solid. (1.5 g, 99%) LC/MS analysis method 7, mass (ES+) m/z 240.2 1H NMR (DMSO-d6): 13.21 (1H, brs), 8.15 (1H, s), 4.18 (4H, brs), 3.72 (4H, t)

Workup

  1. customformed
  2. filtrationthe precipitate was filtered
  3. customUpon drying under high vacuum

Sources & evidence

ORD record
ord-9ebf73700f084cdab961e79ce0514d9e
Source dataset
uspto-grants-2015_03
Patent number
US08987257B2

Reaction notes

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