Methyl iodide → 4-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester

HRID 2098682Notes

Reaction equation

HRID 2098682 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[S:23][C:22]3[C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:20][C:19]([Cl:30])=[N:18][C:17]=3[CH:16]=2)([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:34]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:15]2[S:23][C:22]3[C:21]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)=[N:20][C:19]([Cl:30])=[N:18][C:17]=3[CH:16]=2)([O:14][CH3:34])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58441736HCID 58441736, compound

Product 1

HCID 866530974-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (335 mg) in DMF (3 ml) was added sodium hydride (60% w/w suspension in mineral oil, 41 mg) at 0° C. After 30 min, iodomethane (56 ul) was added and the reaction mixture was warmed slowly to room temperature overnight. Ethyl acetate/brine extraction and purification on silica afforded 4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester (219 mg).

Workup

  1. extractionEthyl acetate/brine extraction and purification on silica

Sources & evidence

ORD record
ord-f8877653ffd74c67995ca0b2cebcc783
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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