Sodium hydride → HCID 21059960, compound

HRID 1241371Notes

Reaction equation

HRID 1241371 reaction equation
[O:1]=[S:2]1(=[O:15])[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=2)[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:19]1[S:20][C:21]([C:24]#[N:25])=[CH:22][N:23]=1>>[O:15]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][C:19]3[S:20][C:21]([C:24]#[N:25])=[CH:22][N:23]=3)[CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21059980HCID 21059980, compound

Product 1

HCID 21059960HCID 21059960, compound

Procedure

6-(1,1-Dioxidothiomorpholin-4-yl)pyrimidin-4-amine 8-2 (0.237 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 preparative hplc column and isolated via lyophilization to yield 8-3. Hi-Res MS: calc: 337.0536 found: 337.0530. 1NMR(DMSO): 8.51 ppm (s, 1H); 8.27 ppm (s, 1H); 6.36 ppm (s, 1H); 4.05 ppm (s, 4H); 3.21 ppm (s, 4H).

Workup

  1. customThe product was purified on a preparative hplc column
  2. customisolated via lyophilization
  3. customto yield 8-3

Sources & evidence

ORD record
ord-e0d60d497a5146d68397040c38f21dfb
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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