Nitrogen → 2,6-dimethyl-3-(6-morpholinopyridin-3-yl)pyrimidin-4(3H)-one

HRID 56151

Reaction equation

HRID 56151 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C[Al](C)C.N#N.[NH:20](/[C:24](/[CH3:30])=[CH:25]\[C:26](OC)=[O:27])[C:21]([CH3:23])=O>C(Cl)Cl>[CH3:23][C:21]1[N:13]([C:10]2[CH:11]=[N:12][C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:8][CH:9]=2)[C:26](=[O:27])[CH:25]=[C:24]([CH3:30])[N:20]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 1040596-(Morpholino)pyridin-3-amineHCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925Trimethylaluminum

Product 1

HCID 729487572,6-dimethyl-3-(6-morpholinopyridin-3-yl)pyrimidin-4(3H)-oneYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-morpholinopyridin-3-amine (1.79 g, 10 mmol) in CH2Cl2 (100 mL) was added trimethylaluminium (40 mL, 40 mmol, 1 M in heptane) carefully under N2. The mixture was stirred at rt for 30 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (1.89 g, 12 mmol) in CH2Cl2 (5 mL). The reaction was stirred at rt for 6 h, then quenched with saturated NH4Cl aqueous solution (100 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by recrystallized from EtOAc to give the title compound as a pale yellow solid (1.11 g, 39%). The compound was characterized by the following spectroscopic data:

Workup

  1. stirringThe reaction was stirred at rt for 6 h
  2. customquenched with saturated NH4Cl aqueous solution (100 mL)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. customby recrystallized from EtOAc

Sources & evidence

ORD record
ord-69d5c9da52714651bccbd451dd45290a
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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