Sodium Bicarbonate → HCID 58550526, compound

HRID 1890988Notes

Reaction equation

HRID 1890988 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].Cl[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:17]=[CH:16][N:15]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH2:27]([O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18]1[N:17]=[CH:16][N:15]=[C:14]([NH:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=2)[CH:19]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27351793-(Methylsulfonyl)aniline hydrochlorideHCID 59840902HCID 59840902, compound

Product 1

HCID 58550526HCID 58550526, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-methanesulfonyl-phenylamine hydrochloride (4.98 g, 24 mmol) and 4-chloro-6-(2-benzyloxyphenyl)-pyrimidine (6.88 g, 23.2 mmol) in DMFA (50 mL) was stirred at 80° C. till the reaction completion (TLC control). The reaction mixture was diluted with water (200 mL), treated with NaHCO3 (4.2 g, 50 mmol). The resulting precipitate was filtered out, washed with water (2×200 mL), dried and purified by column chromatography on silica (eluent chloroform-ethanol 20:1) to yield [6-(2-benzyloxy-phenyl)-pyrimidin-4-yl]-(3-methanesulfonyl-phenyl)-amine as colorless solid.

Workup

  1. filtrationThe resulting precipitate was filtered out
  2. washwashed with water (2×200 mL)
  3. customdried
  4. custompurified by column chromatography on silica (eluent chloroform-ethanol 20:1)

Sources & evidence

ORD record
ord-3a2ad3bc1a1b4456a463df7e2e366630
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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