Methyl iodide → HCID 86618416, compound

HRID 2098753Notes

Reaction equation

HRID 2098753 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][OH:12])=[CH:8][C:6]=2[N:7]=1.[H-].[Na+].[CH3:21]I>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:5]2[S:10][C:9]([CH2:11][O:12][CH3:21])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

Product 1

HCID 86618416HCID 86618416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-methanol (300 mg) in DMF (10 mL) at 0° C. was added sodium hydride (46 mg). The mixture was stirred for 1 h at 0° C. and then methyliodide (0.07 mL) was added. The reaction mixture was stirred at room temperature for 16 h and then quenched with water (20 mL) and extracted into ethyl acetate (2×20 mL). The combined organics were washed with aqueous brine solution (2×20 mL), dried (MgSO4) and concentrated to give 2-chloro-6-methoxymethyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine as a yellow solid (92 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. customquenched with water (20 mL)
  3. extractionextracted into ethyl acetate (2×20 mL)
  4. washThe combined organics were washed with aqueous brine solution (2×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2352f7217f4543b5bbb2a13eaa10ae2b
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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