Methyl iodide → 2-chloro-N-methyl-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-7-amine

HRID 2042238Notes

Reaction equation

HRID 2042238 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[C:6]=2[N:7]=1.[H-].[Na+].I[CH3:27]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([N:11]([CH3:27])[C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 866732242-chloro-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-7-amine

Product 1

HCID 866732252-chloro-N-methyl-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-7-amineYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-7-amine (30 mg, 0.085 mmol) was dissolved in N,N-dimethylformamide (1 mL) and sodium hydride (5.2 mg, 0.13 mmol) was added at 0° C. After stirring for 10 minutes and adding iodomethane (15 mg, 0.10 mmol), the mixture was stirred for an hour, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. The target compound (28 mg, 89% yield) was obtained without purification.

Workup

  1. stirringthe mixture was stirred for an hour
  2. washwashed with brine
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered with celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a0d80f92b83404c95f3a36b54f48c1b
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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