Diisopropylethylamine → 2-chloro-N-[3-(methylsulfinyl)benzyl]-5-(trifluoromethyl)pyrimidin-4-amine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([CH3:19])(=O)=[O:17])[CH:11]=2)[C:5]([C:20]([F:23])([F:22])[F:21])=[CH:4][N:3]=1.ClC1N=C(Cl)C(C(F)(F)F)=CN=1.Cl.CS(C1C=C(CN)C=CC=1)=O.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([CH3:19])=[O:17])[CH:11]=2)[C:5]([C:20]([F:22])([F:21])[F:23])=[CH:4][N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Prepared according to the procedure described above for 2-chloro-N-[3-(methylsulfonyl)benzyl]-5-(trifluoromethyl)pyrimidin-4-amine (XLIVa) using 2,4-dichloro-5-trifluoromethylpyrimidine (XL, 324 mg, 1.5 mmol), 1-[3-(methylsulfinyl)phenyl]methanamine hydrochloride (249 mg, 1.2 mmol) and diisopropylethylamine (0.65 mL, 3.75 mmol) in THF (10 mL). Pure desired 2-chloro-N-[3-(methylsulfinyl)benzyl]-5-(trifluoromethyl)pyrimidin-4-amine (XLVa, 162 mg) was isolated as the non-polar component by chromatography eluting with hexane:ethyl acetate 25:75. 1H NMR (DMSO-d6) δ: 8.61 (t, J=5.7 Hz, 1H), 8.44 (s, 1H), 7.67 (s, 1H), 7.49-7.58 (m, 2H), 7.45 (dt, J=6.6, 2.0 Hz, 1H), 4.70 (d, J=5.9 Hz, 2H), 2.72 (s, 3H). 13C NMR (DMSO-d6) δ: 162.59, 158.35, 155.74 (q, J=5 Hz), 146.49, 139.73, 129.47, 129.24, 123.43 (q, J=272 Hz), 122.40, 122.36, 105.16 (q, J=32 Hz), 43.84, 43.23. A HMBC 3-bond correlation is observed between the C4—N-proton at 8.61 ppm and the C5-carbon at ˜105 ppm.
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-52705e84493e47879514ba3747572ec7
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096624B2
Reaction notes
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