Sodium Hydroxide → HCID 86691785, compound

HRID 1500767Notes

Reaction equation

HRID 1500767 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:4]2=[C:3]([C:10]2[N:15]=[C:14](O)[CH:13]=[CH:12][N:11]=2)[CH:2]=1.P(Cl)(Cl)([Cl:19])=O.[OH-].[Na+]>C(OCC)(=O)C>[Cl:19][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([C:3]2[CH:2]=[N:1][N:5]3[CH:6]=[CH:7][N:8]=[CH:9][C:4]=23)[N:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1785164942-(Pyrazolo[1,5-a]pyrazin-3-yl)pyrimidin-4-ol

Product 1

HCID 86691785HCID 86691785, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(pyrazolo[1,5-a]pyrazin-3-yl)pyrimidin-4-ol (Preparation 10b, 150 mg, 0.7 mmol) in phosphorous oxychloride (1.42 mL, 15.51 mmol) was heated overnight at 110° C. After cooling to ambient temperature, the reaction mixture was poured with caution onto water and basified by addition of a 2N aqueous sodium hydroxide solution. Ethyl acetate was then added and the organic phase was separated, washed with water and brine, dried (MgSO4), filtered and evaporated under reduced pressure to yield the title compound (170 mg, 87%) as a solid which was used in the next synthetic step without further purification.

Workup

  1. additionthe reaction mixture was poured with caution onto water
  2. customthe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-53b0bd57eddd440b8d5e1affed9440a3
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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