4-Chloro-2-(1,1-difluoroethyl)pyrimidine → 3-[2-(1,1-Difluoroethyl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796113Notes

Reaction equation

HRID 1796113 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.Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29]([F:32])([F:31])[CH3:30])[N:24]=1>>[F:31][C:29]([C:25]1[N:26]=[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:28]=[CH:23][N:24]=1)([F:32])[CH3:30]

Participants

3

Reactant 2

HCID 221807734-Chloro-2-(1,1-difluoroethyl)pyrimidineHCID 695598483-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Product 1

HCID 695605703-[2-(1,1-Difluoroethyl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Procedure

3-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (567 mg, 1.4 mmol) and 4-chloro-2-(1,1-difluoroethyl)pyrimidine (209 mg, 1.17 mmol) were reacted together as described in Example 39, Step 1. Purification by column chromatography on silica using 3% MeOH/CH2Cl2 gave 3-[2-(1,1-difluoroethyl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine.

Workup

  1. customPurification by column chromatography on silica using 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-df26a0f452b84f729f5f244aab7ad252
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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