Methyl iodide → HCID 86618416, compound
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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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). Suzuki coupling with 2-chloro-6-methoxymethyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (85 mg) was carried out via General Procedure A. Purification using column chromatography gave 314 as a white solid (24 mg). NMR: CDCl3: 3.41 (3 H, s, Me), 3.81-3.89 (4 H, m, CH2), 4.01-4.08 (4 H, m, CH2), 4.70 (2 H, s, CH2), 7.31 (1 H, s, Ar), 7.42 (1 H, t, J 8.25, Ar), 7.50 (1 H, d, J 8.24, Ar), 8.21 (1 H, d, J 7.21, Ar), 8.96 (1 H, s, Ar) and 10.03 (1 H, s, NH). MS: (ESI+): MH+ 382.17
Workup
- stirringThe reaction mixture was stirred at room temperature for 16 h
- customquenched with water (20 mL)
- extractionextracted into ethyl acetate (2×20 mL)
- washThe combined organics were washed with aqueous brine solution (2×20 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b8e99a3da2a4493d9458ab4d8cc25df7
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846929B2
Reaction notes
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