7-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-4-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidine → 2-[3-(2-(Pyridin-4-yl)pyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

HRID 1796061Notes

Reaction equation

HRID 1796061 reaction equation
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][N:15]2[C:18]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)[N:22]=3)=[CH:19][N:20]=[C:14]2[N:13]=1)([O:4][Si](CC)(CC)CC)[CH3:3]>Cl>[N:30]1[CH:29]=[CH:28][C:27]([C:23]2[N:22]=[C:21]([C:18]3[N:15]4[CH:16]=[CH:17][C:12]([C:2]([OH:4])([CH3:1])[CH3:3])=[N:13][C:14]4=[N:20][CH:19]=3)[CH:26]=[CH:25][N:24]=2)=[CH:32][CH:31]=1

Participants

3

Reactant 1

HCID 695602747-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-4-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidine

Product 1

HCID 102684822-[3-(2-(Pyridin-4-yl)pyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

7-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(pyridin-4-yl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidine from above was treated with conc. HCl (10 drops) as described in Example 39 to yield after purification by column chromatography on silica, using 6% MeOH/CH2Cl2 as the eluent, 2-[3-(2-(pyridin-4-yl)pyrimidin-4-yl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol (51 mg, 15%): 1H NMR (360 MHz, d6-DMSO) δ 10.23 (1H, d, J 7.2), 8.98 (1H, d, J 5.5), 8.88 (1H, s), 8.85-8.80 (2H, m), 8.36 (2H, dd, J 4.5, 1.6), 8.14 (1H, d, J 5.5), 7.77 (1H, d, J 7.2), 5.62 (1H, s), 1.55 (6H, s); m/z (ES+) 333 (M+H+).

Workup

  1. customto yield
  2. customafter purification by column chromatography on silica

Sources & evidence

ORD record
ord-26706dd14e3b439394de9e16b9f2340c
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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