2-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-4-chloropyrimidine → 3-[2-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796111Notes

Reaction equation

HRID 1796111 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.[CH2:22]([N:29]1[CH2:34][CH:33]=[C:32]([C:35]2[N:40]=[C:39](Cl)[CH:38]=[CH:37][N:36]=2)[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([N:29]1[CH2:30][CH:31]=[C:32]([C:35]2[N:36]=[C:37]([C:2]3[N:6]4[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]4=[N:4][CH:3]=3)[CH:38]=[CH:39][N:40]=2)[CH2:33][CH2:34]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 221807832-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-4-chloropyrimidineHCID 695598483-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Product 1

HCID 695602343-[2-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)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 (287 mg, 0.77 mmol) and 2-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-4-chloropyrimidine: (266 mg, 0.93 mmol) were reacted together as described in Example 39, Step 1. Purification by column chromatography on silica, using 4-7.5% MeOH/CH2Cl2, gave 3-[2-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine: m/z (ES+) 540 (M+H+).

Workup

  1. customPurification by column chromatography on silica

Sources & evidence

ORD record
ord-9e966c38d9dd42ca80dac803f798219b
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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