Oxalyl chloride → 3-Benzyl-5-tert-butyl-7-chloro-triazolo[4,5-d]pyrimidine

HRID 400974Notes

Reaction equation

HRID 400974 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=O.[CH2:7]([N:14]1[C:18]2[NH:19][C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])=[N:21]C(=O)C=2[N:16]=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+]>ClCCl.CN(C=O)C>[CH2:7]([N:14]1[C:18]2[N:19]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[N:21]=[C:1]([Cl:6])[C:2]=2[N:16]=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 178441863HCID 178441863, compound

Product 1

HCID 866833853-Benzyl-5-tert-butyl-7-chloro-triazolo[4,5-d]pyrimidineYield 114.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

DMF over MS (105 g, 110 ml, 1.43 mol, Eq: 2.56) was charged in the reactor followed by Dichlormethane (1.46 kg, 1.1 l). The solution was heated to 35° C. and oxalylchloride (144 g, 97.6 ml, 1.11 mol, Eq: 2) was added over 1 h. After 45 min, a fine suspension of 3-benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(4H)-one (161 g, 557 mmol, Eq: 1.00) in a mixture of dichlormethane (877 g, 662 ml) and DMF (41.8 g, 44.1 ml) was added over of 20 min. After 3 h, the reaction mixture was cooled to RT and slowly added to a cold (0-5° C.) half saturated aqueous NaHCO3 (1.76 l). The organic phase was separated and washed again with half saturated NaHCO3 (662 ml) followed by water (662 g, 662 ml). Then the org. phase was dried over MgSO4 and was concentrated under reduced pressure at 50° C./down to 10 mbar to give 192 g of a crude oil which does crystallize on standing. The crude 3-benzyl-5-tert-butyl-7-chloro-triazolo[4,5-d]pyrimidine was introduced in the next step without further purification.

Workup

  1. additionwas added over of 20 min
  2. waitAfter 3 h
  3. temperaturethe reaction mixture was cooled to RT
  4. customThe organic phase was separated
  5. washwashed again with half saturated NaHCO3 (662 ml)
  6. dry with materialphase was dried over MgSO4
  7. concentrationwas concentrated under reduced pressure at 50° C./down to 10 mbar

Sources & evidence

ORD record
ord-34f6758c701d46b7a7310041961ac7f3
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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