Water → Ethyl 2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxylate
Reaction equation
[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[C:9]1[N:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=1.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[S:30](Cl)(=[O:32])=[O:31].O>N1C=CC=CC=1>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[S:30]([N:7]1[CH2:6][CH:5]2[CH2:1][N:2]([C:9]3[N:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=3)[CH2:3][CH:4]2[CH2:8]1)(=[O:31])=[O:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of ethyl 2-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylpyrimidine-5-carboxylate (0.271 g, 1.0 mmol) in pyridine (5 ml) was added 2-naphthalene sulfonyl chloride (0.269 g, 1.18 mmol). The mixture was stirred for 3 h, then water (25 ml) was added and the product collected by filtration. The product was washed with further water and then dried overnight under vacuum to give the title compound (0.231 g, 51%). 1H NMR (300 MHz, CDCl3) δ: 1.39 (3H, t, J=6.9 Hz), 2.92-3.07 (2H, m), 3.29 (2H, dd, J=3.9, 10.2 Hz), 3.45 (2H, dd, J=3.9, 12.3 Hz), 3.59 (2H, dd, J=7.2, 10.2 Hz), 4.35 (2H, q, J=7.2 Hz), 7.58-7.75 (2H, m), 7.82 (1H, dd, J=1.8, 8.7 Hz), 7.90-8.05 (2H, m), 8.40 (1H, s), 8.77 (2H, s).
Workup
- filtrationthe product collected by filtration
- washThe product was washed with further water
- customdried overnight under vacuum
Sources & evidence
- ORD record
- ord-2c9cf785a86747839459c19e64d4f0fd
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932246B2
Reaction notes
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