Water → HCID 71765537, compound

HRID 2272964Notes

Reaction equation

HRID 2272964 reaction equation
Cl[CH2:2][C:3]1[CH:23]=[C:6]2[C:7](=[O:22])[NH:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)=[CH:10][N:5]2[N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:2][C:3]1[CH:23]=[C:6]2[C:7](=[O:22])[NH:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=3)=[CH:10][N:5]2[N:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 71765536HCID 71765536, compound

Product 1

HCID 71765537HCID 71765537, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 18.9 mg (0.055 mmol) 2-chloromethyl-6-(4-trifluoromethoxy-phenyl)-5H-pyrazolo[1,5-a]pyrazin-4-one in 0.5 ml THF is flushed with nitrogen. 3.5 mg (0.092 mmol) Lithiumaluminiumhydride is added and the reaction mixture is stirred for 5 hours at room temperature. Then 1 ml THF, 3.5 μl water, 3.5 μl 15% aqueous NaOH solution and 10.5 μl water are added successively. The resulting suspension is stirred for 30 minutes at room temperature. The precipitate is filtered off and washed with THF and ethanol. The filtrate is evaporated and purified by preparative HPLC to give 2-methyl-6-(4-trifluoromethoxy-phenyl)-5H-pyrazolo[1,5-a]pyrazin-4-one as colourless crystals; HPLC/MS 2.53 min (B), [M+H] 310;

Workup

  1. stirringThe resulting suspension is stirred for 30 minutes at room temperature
  2. filtrationThe precipitate is filtered off
  3. washwashed with THF and ethanol
  4. customThe filtrate is evaporated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2056aa1e3a7d4d1781ee29e2e9405795
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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