Methyl iodide → 3-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloro-1-methyl pyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione

HRID 60161Notes

Reaction equation

HRID 60161 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[CH:19]=[C:20]([Cl:23])[N:21]=[CH:22][C:15]=2[NH:14][C:13]1=[O:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:25]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O.CC(=O)OCC.O>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[CH:19]=[C:20]([Cl:23])[N:21]=[CH:22][C:15]=2[N:14]([CH3:25])[C:13]1=[O:24])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1317370813-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1317370803-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloro-1-methyl pyrido[3,4-d]pyrimidine-2,4(1H,3H)-dioneYield 87.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (3.3 g, 0.0089 mol), K2CO3 (2.468 g, 0.0178 mol) in acetone (10 mL) was added iodomethane (1.51 g, 0.01 mmol). The reaction was stirred at RT for 3 h then diluted with EA (20 mL) and water (5 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated to give 3-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloro-1-methyl pyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (3 g, 87% yield) as a white solid. MH+ 384, TR=2.166 min. Used without further purification.

Workup

  1. washThe organic layer was washed with brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1db88439011948659afec1c0d52e5c0d
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

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