N,N-Dimethylaniline → 4-Chloro-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1500456Notes

Reaction equation

HRID 1500456 reaction equation
O=P(Cl)(Cl)[Cl:3].CN(C)C1C=CC=CC=1.O[C:16]1[N:21]=[C:20]([S:22][CH3:23])[N:19]=[C:18]2[NH:24][N:25]=[C:26]([CH3:27])[C:17]=12>>[Cl:3][C:16]1[N:21]=[C:20]([S:22][CH3:23])[N:19]=[C:18]2[NH:24][N:25]=[C:26]([CH3:27])[C:17]=12

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178503516HCID 178503516, compound

Product 1

HCID 1785034684-Chloro-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

Procedure

To a mixture of POCl3 (26 mL) and of dimethylaniline (2 mL) was added crude 4-hydroxy-3-methyl-6-methylmercaptopyrazolo[3,4-d]pyrimidine (A-2) (1.46 g, 7.45 mmol). The solution was heated to reflux for 60 min until all solid dissolved. The excess of POCl3 was removed under reduced pressure. The residue was poured into ice water with vigorous stirring, it is stirred for 10 min, and the aqueous solution was extracted with ether. The ether layer was washed with cold water, dried with anhydrous Na2SO4 and concentrated to give the title compound (A-3) (1.21 g, 5.63 mmol). MS-ESI (m/z): 215.0 (M+H)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 60 min until all solid
  3. dissolutiondissolved
  4. customThe excess of POCl3 was removed under reduced pressure
  5. additionThe residue was poured into ice water with vigorous stirring, it
  6. extractionthe aqueous solution was extracted with ether
  7. washThe ether layer was washed with cold water
  8. dry with materialdried with anhydrous Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1e70bb859fc341f6bdf510ce67c7e1b8
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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