Water → 6-(Phenethylamino)-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carbonitrile

HRID 2268429Notes

Reaction equation

HRID 2268429 reaction equation
[C-:1]#[N:2].[K+].CS([C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:10]([NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:9]=1)(=O)=O.O>CN(C)C=O>[CH2:24]([NH:23][C:10]1[N:9]=[C:8]([C:1]#[N:2])[N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium Cyanide2×HCID 20709190HCID 20709190, compound

Product 1

HCID 207091976-(Phenethylamino)-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carbonitrileYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium cyanide (5.6 g, 86.2 mmol) was added to a stirred solution of 2-(methylsulfonyl)-N-phenethyl-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine (21.0 g, 43.1 mmol) (preparation 43) in N,N-dimethylformamide (100 ml). The reaction mixture was heated at 110° C. for 74 hr with extra potassium cyanide being added at 44 hr (3.3 g, 50.8 mmol) and 68 hr (1.2 g, 18.5 mmol). The reaction mixture was allowed to stand at room temperature for 70 hr, then poured into water (500 ml), extracted with diethyl ether (1000 ml) and the aqueous layer washed with diethyl ether (500 ml). The combined organic layers were washed with water (3×500 ml). The solvent was removed under reduced pressure from the combined organic layers to give a residue which was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99:1) to give the title compound (10.2 g) as a brown solid. MS: 349 (MH+).

Workup

  1. additionadded at 44 hr (3.3 g, 50.8 mmol) and 68 hr (1.2 g, 18.5 mmol)
  2. extractionextracted with diethyl ether (1000 ml)
  3. washthe aqueous layer washed with diethyl ether (500 ml)
  4. washThe combined organic layers were washed with water (3×500 ml)
  5. customThe solvent was removed under reduced pressure from the combined organic layers
  6. customto give a residue which
  7. customwas purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99:1)

Sources & evidence

ORD record
ord-d82b945b59104859b57c1488fbaf0ce1
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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