Potassium hydroxy sulfite → HCID 52950603, compound

HRID 1966710Notes

Reaction equation

HRID 1966710 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[CH:13][C:12]([CH3:15])=[N:11]2)=[C:6]([CH:9]=1)[CH:7]=O.[NH2:16][C:17]1[N:22]=[CH:21][C:20]([C:23]2[CH:24]=[C:25]([NH2:34])[C:26]([NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:27][CH:28]=2)=[CH:19][N:18]=1.OOS([O-])=O.[K+]>O>[C:30]([N:29]1[C:26]2[CH:27]=[CH:28][C:23]([C:20]3[CH:19]=[N:18][C:17]([NH2:16])=[N:22][CH:21]=3)=[CH:24][C:25]=2[N:34]=[C:7]1[C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N:10]1[CH:14]=[CH:13][C:12]([CH3:15])=[N:11]1)([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 58541966HCID 58541966, compound

Product 1

HCID 52950603HCID 52950603, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A 10 mL aliquot of 5-chloro-2-(3-methyl-pyrazol-1-yl)-benzaldehyde from the above reaction is filtered (in DMF, 50% pure by LC-MS, calculated mass based on purity is 235 mg, 1.10 mmol). The crude aldehyde is treated with 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (200 mg, 0.78 mmol). Oxone (478 mg, 0.78 mmol) is added as a water solution (2 mL). The resulting mixture is warmed to 60° C. for 2 hours and cooled to room temperature. The reaction mixture is 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) followed by mass triggered HPLC(CH3CN/H2O) affords the title compound (45 mg, 13%). LCMS (ESMS): m/z 458.20 (M++1)

Workup

  1. filtrationis filtered (in DMF, 50% pure by LC-MS, calculated mass based on purity is 235 mg, 1.10 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-a7efbc70aa59400183a495b4ec3d3d1a
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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