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

HRID 1453223Notes

Reaction equation

HRID 1453223 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]1

Participants

4

Reactant 3

HCID 43541347-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 587624916-cyclopentyl-6-{2-[4-(difluoromethyl)-3-fluorophenyl]ethyl}-dihydro-2H-pyran-2,4(3H)-dioneHCID 178526943HCID 178526943, compound

Product 1

HCID 587624677-[(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

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. 1H NMR (300 MHz, DMSO-D6) δ 1.55 (m, 8H) 1.94 (m, 2H) 2.33 (m, 1H) 2.44 (d, J=1.7 Hz, 2H) 2.58 (s, 3H,) 2.58 (1H buried under singlet) 2.71 (d, J=18.0 Hz, 1H) 3.38 (dd, J=15.0, 6.0 Hz, 2H) 5.77 (s, 1H) 6.90 (m, 1H) 7.10 (m, 3H) 7.27 (s, 1H) 7.44 (t, J=7.74 Hz, 1H). MS (APCI) calcd for C27H27F3N2O4S: 532.16; found (M+H+) 533.0.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-c28d662e282c4944877256ef7baab221
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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