HCID 21906247, compound → HCID 89486133, compound
Reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.C([Li])CCC.Cl[C:19]([CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)=[O:20]>C1COCC1>[N:12]1[CH:11]=[CH:10][CH:9]=[N:8][C:7]=1[C:2]1([C:19]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[O:20])[S:3][CH2:4][CH2:5][CH2:6][S:1]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-(1,3-dithian-2-yl)pyrimidine (0.583 g, 2.94 mmol) in THF (50 ml) was added n-butyllithium (1.679 ml, 4.20 mmol, 2.5 M) by syringe at −78° C. The mixture was stirred at −78° C. for 0.5 h. Then tert-Butyl 4-(chlorocarbonyl)-piperidine-1-carboxylate (0.52 g, 2.1 mmol) in THF was added via syringe, and the mixture was stirred at −78° C. for 1 h. The reaction was quenched with aqueous NH4Cl, and diluted with ethyl acetate. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated. The resulting crude material was purified on a silica gel column (ethyl acetate/hexane) to give the title compound. LC-MS m/e 354.08 [M+1−56]+.
Workup
- stirringthe mixture was stirred at −78° C. for 1 h
- customThe reaction was quenched with aqueous NH4Cl
- additiondiluted with ethyl acetate
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe resulting crude material was purified on a silica gel column (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-f3b8a5b4fa9547d281cd8658106575fc
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006268B2
Reaction notes
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