Sodium Azide → 4-[4-(4-Azido-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]phenol

HRID 1788025Notes

Reaction equation

HRID 1788025 reaction equation
Cl[C:2]1[C:3]2[S:23][CH2:22][CH2:21][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([C:2]1[C:3]2[S:23][CH2:22][CH2:21][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1)=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866162784-[4-(4-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]phenol

Product 1

HCID 866162794-[4-(4-Azido-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]phenolYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.18 g (2.75 mmol) of 4-[4-(4-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]phenol (III) is placed in 25 mL of dimethylformamide, and 1.20 g (18.46 mmol) of sodium azide is added. The reaction mixture is stirred for 4.5 hours at 100° C. Then it is concentrated by evaporation, and the residue is cooled in the ice bath and combined with water. The precipitate formed is suction filtered, washed, and dried. 0.800 g of product IV is obtained and used further as a crude product.

Workup

  1. concentrationThen it is concentrated by evaporation
  2. temperaturethe residue is cooled in the ice bath
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-0326a1ec94354c539191d9963459185c
Source dataset
uspto-grants-2009_03
Patent number
US07511045B2

Reaction notes

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