Methyl vinyl sulfone → HCID 59239445, compound
Reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH3:29])[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[CH3:30][S:31]([CH:34]=[CH2:35])(=[O:33])=[O:32].CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH3:29])[C:16]3[CH2:22][CH2:21][N:20]([CH2:35][CH2:34][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (ca) (0.35 mmol), methyl-sulfonylethene (3.5 mmol), DIPEA (1 mL), in a mixed solvent of THF/DMF (30 mL, 10:1) was stirred at 40° C. overnight. The solvent was removed in vacuum and the residue was purified by preparative TLC (Hexanes:ethyl acetate=1:2) to give 48.2 mg (yield: 27%) of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-7-(2-(methylsulfonyl)ethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (yg). 1H NMR (D6-DMSO, 400 MHz): δ 8.60 (s, 1H), 8.13 (d, J=7.2, 2H), 7.44 (d, J=7.2, 2H), 6.12 (t, J=2.5, 1H), 4.18-3.33 (m, 11H), 3.19-2.63 (m, 11H), 1.20 (d, J=6.8, 3H), 1.04 (t, J=7.2, 3H). LC-MS: m/z=+503 (M+H)+.
Workup
- customThe solvent was removed in vacuum
- customthe residue was purified by preparative TLC (Hexanes:ethyl acetate=1:2)
Sources & evidence
- ORD record
- ord-070500073570444abd20df992e7924c1
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163763B2
Reaction notes
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