7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one → 7-[(6-Cyclopentyl-6-{2-[4-(difluoromethyl)-3-fluorophenyl]ethyl}-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl)methyl]-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]([F:24])[F:23])=[C:18]([F:25])[CH:17]=3)[O:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:27][C:28]1[N:29]=[C:30]2[S:37][CH:36]=[C:35]([CH3:38])[N:31]2[C:32](=[O:34])[CH:33]=1.O.OC1N=CN=C2C=1NC(S)=N2>>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]([F:24])[F:23])=[C:18]([F:25])[CH:17]=3)[O:11][C:10](=[O:12])[C:9]([CH2:27][C:28]3[N:29]=[C:30]4[S:37][CH:36]=[C:35]([CH3:38])[N:31]4[C:32](=[O:34])[CH:33]=3)=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared as described in Example B(54) where 6-Cyclopentyl-6-{2-[4-(difluoromethyl)-3-fluorophenyl]ethyl}-dihydro-2H-pyran-2,4(3H)-dione (described in Step 3 of Example B(69)) was used in place of 6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione and 7-(Chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (prepared according to a reported procedure: Doria, G.; Passarotti, C.; Sala, R.; Magrini, R.; Sberze, P.; Tibolla, M.; Cesarani, R.; Arcari, G.; Castello, R.; Toti, D. Farmaco Ed. Sci. 1985, 40, 885) was used in place of 6-Hydroxy-8-mercaptopurine monohydrate.
Workup
- customprepared
Sources & evidence
- ORD record
- ord-af70aac9f05e454cb40809d859f4c624
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148226B2
Reaction notes
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