7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one → 7-[(6-{2-[3-Chloro-4-(cyclopropylmethoxy)phenyl]ethyl}-6-cyclopentyl-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 1453190Notes

Reaction equation

HRID 1453190 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[S:12][CH:11]=[C:10]([CH3:13])[N:6]2[C:7](=[O:9])[CH:8]=1.ClCC1N(C)N=C(C)N=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH2:35][CH2:36][C:37]2([CH:45]3[CH2:49][CH2:48][CH2:47][CH2:46]3)[O:42][C:41](=[O:43])[CH2:40][C:39](=[O:44])[CH2:38]2)[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH:32]1[CH2:34][CH2:33]1>O>[Cl:23][C:24]1[CH:25]=[C:26]([CH2:35][CH2:36][C:37]2([CH:45]3[CH2:49][CH2:48][CH2:47][CH2:46]3)[O:42][C:41](=[O:43])[C:40]([CH2:2][C:3]3[N:4]=[C:5]4[S:12][CH:11]=[C:10]([CH3:13])[N:6]4[C:7](=[O:9])[CH:8]=3)=[C:39]([OH:44])[CH2:38]2)[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH:32]1[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 43541347-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 131031005-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazoleHCID 587626706-[2-(3-Chloro-4-cyclopropylmethoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione

Product 1

HCID 587626037-[(6-{2-[3-Chloro-4-(cyclopropylmethoxy)phenyl]ethyl}-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl)methyl]-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as described in Example B(53), using 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) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole and using 6-{-[3-chloro-4-(cyclopropylmethoxy)phenyl]ethyl}-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione (from Step 4, below) in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 1%. 1H NMR (300 MHz, DMSO-d6) □ 0.31 (m, 2H), 0.56 (m, 2H), 1.22 (m, 1H), 1.23-1.65 (m, 8H), 1.92 (m, 2H), 2.33 (m, 1H), 2.48-2.75 (s, m, 7H, overlap with DMSO-d5), 3.45 (m, 2H, overlap with H2O peak), 3.84 (d, J=7.8 Hz, 2H), 4.87 (s, 2H), 5.20 (s, 1H), 6.16 (s, 1H), 6.93 (d, J=9 Hz, 1H), 7.01 (dd, J=9, 1.5 Hz, 1H), 7.18 (d, J=1.5 Hz, 1H). LC-MS (APCI) calcd for C30H33ClN2O5S: 568.18; found (M+H+) 569.0 m/z.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-c3d61f33885d4faca06c136a8a6f1da5
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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