Sodium Bicarbonate → HCID 21258203, compound

HRID 635216Notes

Reaction equation

HRID 635216 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][C:23]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)(O)[CH2:22][CH2:21]2)[CH:17]=[C:16]([CH3:32])[N:15]=1)[CH2:12][CH3:13].C(=O)([O-])O.[Na+]>C(O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[CH:5]=[CH:4][C:3]=1[N:11]([C:14]1[N:19]=[C:18]([N:20]2[CH2:21][CH:22]=[C:23]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)[CH2:24][CH2:25]2)[CH:17]=[C:16]([CH3:32])[N:15]=1)[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 21258219HCID 21258219, compound

Product 1

HCID 21258203HCID 21258203, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2-[N-(2-Bromo-4-isopropylphenyl)-N-ethylamino]-4-[4-(thiophen-2-yl)-4-hydroxypiperidin-1-yl]-6-methylpyrimidine (166 mg) was stirred in 0.5 ml of99% formic acid at room temperature for 2 hours. The reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The extract was washed successively with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The desiccant was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1) to give 132 mg of 2- [N- (2-bromo-4-isopropylphenyl) -N-ethylamino] -4-[4-(thiophen-2-yl)-1,2,3,6-tetrahydropyridin-1-yl]-6-methylpyrimidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with a saturated sodium hydrogencarbonate aqueous solution
  3. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-d80ca4b601e14394aebf9dde22bd8fe8
Source dataset
uspto-grants-2001_02
Patent number
US06187781B1

Reaction notes

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