Morpholine → HCID 59540935, compound

HRID 1677517Notes

Reaction equation

HRID 1677517 reaction equation
[CH3:1][C:2]([CH3:37])([C:6](=[O:36])[C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[N:14]=2)[N:9]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:8]=1)[CH2:3][CH:4]=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH3:1][C:2]([CH3:37])([CH2:3][CH2:4][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)[C:6]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)[N:14]=2)[N:9]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:33])[CH3:34])[CH:8]=1)=[O:36]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59540712HCID 59540712, compound

Product 1

HCID 59540935HCID 59540935, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of crude 3,3-dimethyl-4-oxo-4-[2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyraldehyde (0.161 g, 0.305 mmol), morpholine (0.029 mL, 0.34 mmol), and sodium triacetoxyborohydride (0.129 g, 0.610 mmol) in 3 mL of 1,2-dichloroethane was stirred for 15 h. A sat. aq. NaHCO3 solution (10 mL) was added, and the mixture stirred for 10 min. The layers were separated, and the aqueous layer was extracted with two 20 mL portions of ethyl acetate. The three combined organic layers were dried over MgSO4, filtered, and concentrated to a residue. Column chromatography (0→10% MeOH/CH2Cl2) afforded 0.024 g (13%) of 2,2-dimethyl-4-morpholin-4-yl-1-[2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butan-1-one as a brown oil.

Workup

  1. stirringthe mixture stirred for 10 min
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with two 20 mL portions of ethyl acetate
  4. dry with materialThe three combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-20ddb68d3fd840ae8e9c02b80ed7aa5a
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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