(+-)-2-Butanol → HCID 42633116, compound

HRID 1408475Notes

Reaction equation

HRID 1408475 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[NH2:28][NH2:29].[CH:30]([OH:34])(CC)[CH3:31]>>[F:19][C:18]([F:21])([F:20])[O:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:6]2[N:5]=[CH:4][N:3]=[C:2]3[N:28]([CH2:31][CH2:30][OH:34])[N:29]=[CH:8][C:7]=23)=[CH:12][CH:13]=1.[F:19][C:18]([F:21])([F:20])[O:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:6]2[C:7]3[C:2](=[N:28][N:29]([CH2:31][CH2:30][OH:34])[CH:8]=3)[N:3]=[CH:4][N:5]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6568(+-)-2-ButanolHCID 9321HydrazineHCID 10340Sodium CarbonateHCID 49780776HCID 49780776, compound

Product 2

HCID 42633116HCID 42633116, compoundHCID 42633666HCID 42633666, compound

Conditions

Temperature
60 °C

Procedure

To solution of 4-chloro-6-(4-trifluoromethoxy-phenylamino)-pyrimidine-5-carbaldehyde (50 g, 0.15 mmol) in sec-BuOH was added Na2CO3 (30 mg, 0.26 mmol) and hydrazine (20 mg, 0.18 mmol). The reaction was stirred at 60° C. temperature for 8 hours. The reaction mixture was partitioned in 100 ml water and 100 ml ethyl acetate, extracted with ethyl acetate three times. The organic phase was combined and washed with brine, dried over Na2SO4. The crude product was purified by silica gel flash chromatography by using hexane:ethyl acetate as eluent resulting 2-(4-(4-(trifluoromethoxy)phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethanol and 2-(4-(4-(trifluoromethoxy)phenylamino)-2H-pyrazolo[3,4-d]pyrimidin-2-yl)ethanol in the ratio of 4:1 as yellow solids.

Workup

  1. customThe reaction mixture was partitioned in 100 ml water
  2. extraction100 ml ethyl acetate, extracted with ethyl acetate three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-6db0e0b9da444a9f88f845a4df39ab3f
Source dataset
uspto-grants-2014_12
Patent number
US08921336B2

Reaction notes

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