Sodium hydride → HCID 21934616, compound

HRID 1241376Notes

Reaction equation

HRID 1241376 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][N:19]=[C:18]([NH2:22])[CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:26]1[S:27][C:28]([C:31]#[N:32])=[CH:29][N:30]=1>>[N:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][N:19]=[C:18]([NH:22][C:26]4[S:27][C:28]([C:31]#[N:32])=[CH:29][N:30]=4)[CH:17]=3)[CH2:12][CH2:11]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934643HCID 21934643, compound

Product 1

HCID 21934616HCID 21934616, compound

Procedure

6-[4-(3-Morpholin-4-ylpropyl)piperazin-1-yl]pyrimidin-4-amine 10-2 (0.317 g, 1.04 mmol), sodium hydride (0.083 g, 2.08 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.15 g, 1.04 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: 415.2023 found: 415.2030. 1NMR (CD3OD): 8.48 ppm (s, 1H); 8.02 ppm (s, 1H); 6.27 ppm (s, 1H); 3.94 ppm (m, 6H); 3.43–3.27 ppm (m, 14H); 2.29 ppm (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-63a5d6af4b2043c28f63b751dad22629
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…