Potassium hydroxy sulfite → HCID 53236491, compound

HRID 1966711Notes

Reaction equation

HRID 1966711 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=2[CH:8]=O)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:18][C:19]1[N:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([NH2:36])[C:28]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:29][CH:30]=2)=[CH:21][N:20]=1.OOS([O-])=O.[K+]>O>[C:32]([N:31]1[C:28]2[CH:29]=[CH:30][C:25]([C:22]3[CH:21]=[N:20][C:19]([NH2:18])=[N:24][CH:23]=3)=[CH:26][C:27]=2[N:36]=[C:8]1[C:7]1[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=[CH:13][C:6]=1[N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 58541946HCID 58541946, compound

Product 1

HCID 53236491HCID 53236491, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A 6 mL aliquot of 2-pyrazol-1-yl-5-trifluoromethyl-benzaldehyde from the above reaction is filtered (in DMF, 50% pure by LC-MS, calculated mass based on purity is 98 mg, 0.41 mmol). The crude aldehyde is treated with 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (100 mg, 0.39 mmol). Oxone (239 mg, 0.39 mmol) is added as a water solution (1 mL). The resulting mixture is warmed to 60° C. for 2 hours and cooled to room temperature, poured into water and extracted with EtOAc (3×). The combined organics are dried (MgSO4), filtered, and concentrated. Purification via flash chromatography (12 g silica gel, 0-6% MeOH/CH2Cl2) follows by mass triggered HPLC (CH3CN/H2O) affords the title compound (40 mg, 22%). LCMS (ESMS): m/z 478.20 (M++1)

Workup

  1. filtrationis filtered (in DMF, 50% pure by LC-MS, calculated mass based on purity is 98 mg, 0.41 mmol)
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organics are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash chromatography (12 g silica gel, 0-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-672ea8c335a94151b754c276f3eda0be
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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