Triethylamine → 2-(1,3,4,6,7,11b-Hexahydro-pyrazino[2,1-a] isoquinolin-2-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1045650Notes

Reaction equation

HRID 1045650 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:3]=1.[CH2:16]1[CH:21]2[C:22]3[C:27]([CH2:28][CH2:29][N:20]2[CH2:19][CH2:18][NH:17]1)=[CH:26][CH:25]=[CH:24][CH:23]=3.C(N(CC)CC)C>CN(C)C=O>[CH2:16]1[CH:21]2[C:22]3[C:27]([CH2:28][CH2:29][N:20]2[CH2:19][CH2:18][N:17]1[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:3]=1)=[CH:26][CH:25]=[CH:24][CH:23]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179345AzaquinzoleHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-

Product 1

HCID 578699502-(1,3,4,6,7,11b-Hexahydro-pyrazino[2,1-a] isoquinolin-2-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (332 mg, 1.5 mmol) was added to the solution of 1,3,4,6,7,11b-hexahydro-2H-pyrazino[2,1-a]isoquinoline (292 mg, 1.55 mmol), triethylamine (0.223 ml, 1.6 mmol) in N,N-dimethylformamide (8 ml) and the mixture was stirred for 6 hours and stood overnight ice-water. After addition of ice-water the solution was partitioned between water and ethyl acetate, and the organic layer was washed with brine and dried with magnesium sulfate. The solvents were removed under reduced pressure and purification by silica gel column chromatography (eluent; dichloromethane/methanol=95/5) afforded title compound (530 mg, 95%). Treatment with 4N hydrogen chloride in ethyl acetate yielded corresponding hydrogen chloride salt (495 mg).

Workup

  1. waitstood overnight
  2. customwas partitioned between water and ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvents were removed under reduced pressure and purification by silica gel column chromatography (eluent; dichloromethane/methanol=95/5)

Sources & evidence

ORD record
ord-a6c101f50b374171bb7e42a4315bdc6e
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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