Morpholine → HCID 118024045, compound

HRID 2171812Notes

Reaction equation

HRID 2171812 reaction equation
[CH:1]1([C:7]2[S:19][C:10]3[N:11]=[C:12]([CH3:18])[N:13]=[C:14](/[CH:15]=[CH:16]\O)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+]>CC(O)=O>[CH:1]1([C:7]2[S:19][C:10]3[N:11]=[C:12]([CH3:18])[N:13]=[C:14]([CH2:15][CH2:16][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 136951116HCID 136951116, compound

Product 1

HCID 118024045HCID 118024045, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of (Z)-2-(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)ethenol (120 mg) and AcOH (12 mL) were added morpholine (400 μL) and NaBH (OAc)3 (200 mg), followed by stirring at room temperature for 15 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) to obtain 6-cyclohexyl-2-methyl-4-[2-(morpholin-4-yl)ethyl]thieno[2,3-d]pyrimidine (53 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-7911ec46780b407f9403f959c6f8d6d0
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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