Diethylcarbamoyl chloride → 1-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1896441Notes

Reaction equation

HRID 1896441 reaction equation
[Cl:1][C:2]1[NH:10][CH:9]=[N:8][C:7]2[C:3]=1[N:4]=[CH:5][N:6]=2.O[CH2:12][N:13]1[CH2:17][CH:16]([CH2:18][CH2:19][CH3:20])[CH2:15][C:14]1=[O:21].C(N(CC)C(Cl)=O)C>CC#N>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][N:13]1[CH2:17][CH:16]([CH2:18][CH2:19][CH3:20])[CH2:15][C:14]1=[O:21]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-oneHCID 178478416HCID 178478416, compound

Product 1

HCID 577430091-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-1H-purine x165 (2 g, 12.93 mmol, 1 eq), 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (2.44 g, 15.53 mmol, 1.2 eq) and N,N-diethylcarbamoylchloride (332 mg, 1.293 mmol, 0.1 eq) in MeCN (30 ml) is heated at 100° C. in microwave apparatus during 5 hours. After cooling, the solvent is evaporated and the crude is purified on silicagel (CH2Cl2/MeOH (+NH4OH 10%) 95/5) to yield 3.8 g of 1-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one x166 as a pale yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated
  3. customthe crude is purified on silicagel (CH2Cl2/MeOH (+NH4OH 10%) 95/5)

Sources & evidence

ORD record
ord-541d6e73ab6c4ad0b6fa9ae084a6fc0f
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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