Potassium Carbonate → 1-[(3-Cyano-pyridin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

HRID 44904Notes

Reaction equation

HRID 44904 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([Br:11])[N:7]([CH2:12][C:13]#[C:14][CH3:15])[C:6]=2[C:5](=[O:16])[NH:4][C:3]1=[O:17].C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O.Cl[CH2:32][C:33]1[C:38]([C:39]#[N:40])=[CH:37][CH:36]=[CH:35][N:34]=1>O>[C:39]([C:38]1[C:33]([CH2:32][N:4]2[C:5](=[O:16])[C:6]3[N:7]([CH2:12][C:13]#[C:14][CH3:15])[C:8]([Br:11])=[N:9][C:10]=3[N:2]([CH3:1])[C:3]2=[O:17])=[N:34][CH:35]=[CH:36][CH:37]=1)#[N:40]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 210889278-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dioneHCID 469118343-Pyridinecarbonitrile, 2-(chloromethyl)-

Product 1

HCID 167265441-[(3-Cyano-pyridin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

202 g (0.68 mol) of 3-methyl-7-(2-butin-1-yl)-8-bromoxanthine, 188.5 g (1.36 mol) of anhydrous potassium carbonate and 1.68 liters of N-methyl-2-pyrrolidone are initially charged in the reactor and heated to 70° C. Subsequently, 119 g (0.75 mol) of 2-chloromethyl-3-cyanopyridine in 240 ml of N-methyl-2-pyrrolidine (NMP) are added dropwise. The reactor contents are stirred at 70° C. for 19 hours. After the reaction has ended, 2.8 liters of water are added to the reaction mixture and it is cooled to 25° C. The product is filtered off, washed with 2 liters of water and dried at 70° C. in a drying cabinet under inertization.

Workup

  1. temperatureis cooled to 25° C
  2. filtrationThe product is filtered off
  3. washwashed with 2 liters of water
  4. customdried at 70° C. in a drying cabinet under inertization

Sources & evidence

ORD record
ord-60dba6319e294f8fa885800cce6c66fd
Source dataset
uspto-grants-2013_09
Patent number
US08541450B2

Reaction notes

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