Sodium hydride → tert-Butyl{1-[2-(7-fluoro-3-methyl-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 255299Notes

Reaction equation

HRID 255299 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[N:7]([CH3:13])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26][CH2:25]1)(=O)=O.COC1C=C2C(C=CC(=O)N2CCN2CCC(NC(=O)OC(C)(C)C)CC2)=CC=1>C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[N:7]([CH3:13])[C:8](=[O:12])[N:9]2[CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:32])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateHCID 667752467-Fluoro-3-methylquinazoline-2,4(1H,3H)-dione2×

Product 1

HCID 86642639tert-Butyl{1-[2-(7-fluoro-3-methyl-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-Fluoro-3-methylquinazoline-2,4(1H,3H)-dione [Intermediate 136] (388 mg, 2.0 mmol) was deprotonated with sodium hydride (100 mg, 60% in oil, 2.4 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) 2.75 mmol) as described for Intermediate 2. Chromatography on silica gel using ethyl acetate in hexanes (10-30%) gave the title compound as a yellow oil (200 mg, 24%).

Sources & evidence

ORD record
ord-a090637ece9847f79397df5c62228071
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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