Sodium hydride → 2-({6-[Bis(2-methoxyethyl)amino]pyrimidin-4-yl}amino)-1,3-thiazole-5-carbonitrile

HRID 1241367Notes

Reaction equation

HRID 1241367 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:13][CH2:14][O:15][CH3:16])[C:6]1[CH:11]=[C:10]([NH2:12])[N:9]=[CH:8][N:7]=1.[H-].[Na+].Cl[C:20]1[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=1>>[CH3:16][O:15][CH2:14][CH2:13][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:6]1[N:7]=[CH:8][N:9]=[C:10]([NH:12][C:20]2[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=2)[CH:11]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934632N4,N4-bis(2-methoxyethyl)pyrimidine-4,6-diamine

Product 1

HCID 219347182-({6-[Bis(2-methoxyethyl)amino]pyrimidin-4-yl}amino)-1,3-thiazole-5-carbonitrile

Procedure

N,N-bis(2-methoxyethyl)pyrimidine-4,6-diamine 6-2 (0.13 g, 0.58 mmol), sodium hydride (0.046 g, 1.16 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.083 g, 0.58 mmol) were treated as in Scheme 4 above. The product 6-3 was purified on a C18 preparative hplc column and isolated via lyophilization. Hi-Res MS: calc: 335.1285 found: 335.1282. 1H-NMR (DMSO): 8.39 ppm (s, 1H); 8.24 ppm (s, 1H); 6.22 ppm (s, 1H); 3.65 ppm (m, 4H); 3.51 ppm (m, 4H); 3.26 ppm (s, 6H).

Workup

  1. customThe product 6-3 was purified on a C18 preparative hplc column
  2. customisolated via lyophilization

Sources & evidence

ORD record
ord-3019c6a2fd1d4ca1aadae186474c42b4
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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