Sodium hydride → HCID 21934662, compound

HRID 1241365Notes

Reaction equation

HRID 1241365 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=2)[CH2:7][CH2:6]1.[H-].[Na+].Cl[C:21]1[S:22][C:23]([C:26]#[N:27])=[CH:24][N:25]=1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH:17][C:21]3[S:22][C:23]([C:26]#[N:27])=[CH:24][N:25]=3)[CH:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934672HCID 21934672, compound

Product 1

HCID 21934662HCID 21934662, compound

Procedure

6-[4-(2-methoxyethyl)piperazin-1-yl]pyrimidin-4-amine 5-3 (0.25 g, 1.05 mmol), sodium hydride (0.842 g, 2.11 mmol), and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.15 g, 1.05 mmol) were treated as in Scheme 4 above. The product 5-4 was purified on a C18 preparative hplc and isolated via lyophilization from dioxane. Hi-Res MS: calc: 346.1445 found: 346.1445. 1H-NMR (DMSO): 9.97 ppm (s, 1H); 8.51 ppm (s, 1H); 8.28 ppm (s, 1H); 6.32 ppm (s, 1H); 4.35 ppm (m, 2H); 3.68 ppm (m, 2H); 3.59 ppm (m, 2H); 3.37 ppm (m, 7H); 3.12 ppm (m, 2H).

Workup

  1. customThe product 5-4 was purified on a C18 preparative hplc
  2. customisolated via lyophilization from dioxane

Sources & evidence

ORD record
ord-ae6918cba1284349a598dfcc38d00e3d
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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