Water → 1-[(4-Methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(piperazin-1-yl)-xanthine

HRID 1986523Notes

Reaction equation

HRID 1986523 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][N:13]2[C:22](=[O:23])[C:21]3[N:20]([CH2:24][C:25]#[C:26][CH3:27])[C:19](Br)=[N:18][C:17]=3[N:16]([CH3:29])[C:14]2=[O:15])[N:3]=1.[NH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O.[Cl-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][N:13]2[C:22](=[O:23])[C:21]3[N:20]([CH2:24][C:25]#[C:26][CH3:27])[C:19]([N:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)=[N:18][C:17]=3[N:16]([CH3:29])[C:14]2=[O:15])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 5234Sodium ChlorideHCID 247500498-Bromo-7-but-2-ynyl-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]purine-2,6-dione

Product 1

HCID 113745311-[(4-Methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(piperazin-1-yl)-xanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 300 mg of 1-[(4-methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromoxanthine and 290 mg of piperazine in 5 ml of N,N-dimethylformamide is heated at 200° C. for 5 min in a microwave oven. After cooling to room temperature, the reaction mixture is treated with water and saturated sodium chloride solution and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The solid flask residue is triturated with diethyl ether, filtered off with suction and dried at 45° C. in a circulating air drying oven.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe solid flask residue is triturated with diethyl ether
  7. filtrationfiltered off with suction
  8. customdried at 45° C. in a circulating air
  9. customdrying oven

Sources & evidence

ORD record
ord-4b9f201103714d1f8ff6fb7085877fc7
Source dataset
uspto-grants-2009_06
Patent number
US07550455B2

Reaction notes

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