Sodium hydride → 2-(6-(4-(2-(Pyrrolidin-1-yl)ethyl)piperazin-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

HRID 1241378Notes

Reaction equation

HRID 1241378 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=3)[CH2:10][CH2:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:24]1[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=1>>[N:1]1([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH:20][C:24]4[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=4)[CH:15]=3)[CH2:10][CH2:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 219346496-[4-(2-Pyrrolidin-1-ylethyl)piperazin-1-yl]pyrimidin-4-amine

Product 1

HCID 219346972-(6-(4-(2-(Pyrrolidin-1-yl)ethyl)piperazin-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

Procedure

6-[4-(2-Pyrrolidin-1-ylethyl)piperazin-1-yl]pyrimidin-4-amine 11-2 (0.35 g, 1.27 mmol), sodium hydride (0.101 g, 2.53 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.183 g, 1.27 mmol) were treated as in Scheme 4 above. The product was purified on a C18 preparative column and isolated via lyophilization. Hi-Res MS: calc: 385.1921 found: 385.1918. 1NMR (DMSO): 12.1 ppm (s, 1H); 8.46 ppm (s, 1H); 8.27 ppm (s, 1H); 6.27 ppm (s, 1H); 3.63 ppm (m, 6H); 3.35 ppm (m, 4H); 2.76 ppm (m, 6H); 1.96 ppm (s, 4H).

Workup

  1. customThe product was purified on a C18 preparative column
  2. customisolated via lyophilization

Sources & evidence

ORD record
ord-682a8440279a464a8eee79ea477705cb
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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