Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[C:14]([CH3:28])[O:13][N:12]=1.C(N=C(N(C)C)N(C)C)(C)(C)C.ClCCl>N1C=CC=CC=1>[CH3:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([S:24]([NH:9][C:4]3[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[N:3]=3)(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[C:14]([CH3:28])[O:13][N:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4,6-dimethylpyrimidin-2-amine (84 mg, 0.682 mmol) in pyridine (8 mL), stirred under nitrogen at room temperature, was added 4-((3,5-dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride (346 mg, 1.147 mmol). The reaction mixture was stirred at room temperature overnight. 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.142 mL, 0.682 mmol) was then added to the mixture and the reaction heated by microwaves to 150° C. for 15 minutes. Dichloromethane (DCM) (15 mL) was added to the mixture and the organic phase washed with water (2×25 mL), then dried using a hydrophobic frit. Solvent was removed in vacuo to give the crude product (100 mg) as an orange oil. This was used directly in the next step without further purification. LCMS (2 min, formic) Rt 0.81 min, m/z (ES+) 389 (M+H).
Workup
- temperaturethe reaction heated by microwaves to 150° C. for 15 minutes
- washthe organic phase washed with water (2×25 mL)
- customdried
- customSolvent was removed in vacuo
Sources & evidence
- ORD record
- ord-5240216d45a34e8c89d5973dccdc0452
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242972B2
Linked notes
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