2,4-Diiodopyrimidine → 3-(2-Iodopyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796114Notes

Reaction equation

HRID 1796114 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([CH3:21])([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[I:22][C:23]1[N:28]=[C:27](I)[CH:26]=[CH:25][N:24]=1>>[I:22][C:23]1[N:28]=[C:27]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([CH3:21])([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:12])=[N:10][C:5]3=[N:4][CH:3]=2)[CH:26]=[CH:25][N:24]=1

Participants

3

Reactant 2

HCID 112212422,4-DiiodopyrimidineHCID 695598483-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Product 1

HCID 878893043-(2-Iodopyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidineYield 74.3%

Procedure

3-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (5.0 g, 13.5 mmol) and 2,4-diiodopyrimidine (prepared according to Leprete et al. in Tetrahedron, 2000, 56, 265-273) (5.6 g, 16.9 mmol) were reacted together as described in Example 39, Step 1. Purification by column chromatography on silica using 2.5% MeOH/CH2Cl2 gave 3-(2-iodopyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (4.97 g, 74%): 1H NMR (400 MHz, CDCl3) δ 9.95 (1H, d, J 7.3), 8.47 (1H, s), 8.35 (1H, d, J 5.4), 7.66 (1H, d, J 7.3), 7.59 (1H, d, J 5.4), 1.66 (6H, s), 1.00 (9H, t, J 8.0), 0.67 (6H, q, J 8.0).

Workup

  1. customPurification by column chromatography on silica using 2.5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-ad957fcfc5ff4131a5defd32ebabc932
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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