Diisopropylethylamine → HCID 11260477, compound

HRID 225446Notes

Reaction equation

HRID 225446 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:13]3[N:14]=[C:15]([CH3:19])[N:16]=[C:17](Cl)[C:12]=3[S:11][C:10]=2[CH3:20])=[C:4]([CH3:21])[CH:3]=1.[NH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][OH:29])[CH2:24][CH2:23]1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:13]3[N:14]=[C:15]([CH3:19])[N:16]=[C:17]([N:22]4[CH2:27][CH2:26][CH:25]([CH2:28][OH:29])[CH2:24][CH2:23]4)[C:12]=3[S:11][C:10]=2[CH3:20])=[C:4]([CH3:21])[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4207714-PiperidinemethanolHCID 516892Sodium BicarbonateHCID 57753034HCID 57753034, compound

Product 1

HCID 11260477HCID 11260477, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2,6-dimethyl-thieno[3,2-d]pyrimidine (500 mg), piperidin-4-ylmethanol (226 mg), N,N-diisopropylethylamine (253 mg) in ethanol (1.5 mL) was heated at reflux for 1 day. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate, and then extracted with EtOAc. The organic layer washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/EtOAc=3:1) to obtain {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol as a white solid (568 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 day
  3. extractionextracted with EtOAc
  4. washThe organic layer washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. custompurified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/EtOAc=3:1)

Sources & evidence

ORD record
ord-28b14621cd83466090e5724cfcc4903b
Source dataset
uspto-grants-2009_07
Patent number
US07557111B2

Reaction notes

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