Sodium Methoxide → HCID 67190442, compound
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[S:10][C:9]([CH2:11][S:12][C:13](=O)[CH3:14])=[CH:8][C:6]=2[N:7]=1.C[O-].[Na+].[CH3:25][O:26][CH2:27]CCOS(C1C=CC(C)=CC=1)(=O)=O>CO>[CH3:25][O:26][CH2:27][CH2:14][CH2:13][S:12][CH2:11][C:9]1[S:10][C:5]2[C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[N:3][C:2]([CH3:1])=[N:7][C:6]=2[CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of thioacetic acid S-(2-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl) ester (200 mg) in methanol (10 mL) at 0° C. was added a solution of sodium methoxide (35 mg) in methanol (2 mL). The reaction mixture was stirred at 0° C. for 30 min and then a solution of toluene-4-sulfonic acid 3-methoxy-propyl ester (156 mg) in methanol (3 mL) was added dropwise. 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), concentrated and purified using column chromatography to give 6-(3-methoxy-propylsulfanylmethyl)-2-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine as a white solid (170 mg).
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
- custompurified
Sources & evidence
- ORD record
- ord-1749b63f0d6747148b80a73e754ec45c
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450315B2
Reaction notes
Loading…