2-(Tributylstannyl)furan → 3-[2-(Furan-2-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796062Notes

Reaction equation

HRID 1796062 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([CH3:27])([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:33]1[O:34][CH:35]=[CH:36][CH:37]=1)CCC>>[O:34]1[CH:35]=[CH:36][CH:37]=[C:33]1[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([CH3:27])([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 878895493-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-alpha]pyrimidine

Product 1

HCID 1317257023-[2-(Furan-2-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidineYield 59%

Procedure

3-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-α]pyrimidine (from Example 34) (58 mg, 0.14 mmol) and 2-tributylstannylfuran (102 mg, 0.29 mmol) were heated at reflux overnight as described in Example 40. Purification by column chromatography on silica using 70% EtOAc/isohexanes as the eluent gave 3-[2-(furan-2-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (36 mg, 57%): m/z (ES+) 435 (M+H+).

Workup

  1. temperatureat reflux overnight
  2. customPurification by column chromatography on silica using 70% EtOAc/isohexanes as the eluent

Sources & evidence

ORD record
ord-265a33a3e47e4fa7ab5793272c11ec52
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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