Sodium hydride → 2-(6-(1,4-Diazepan-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

HRID 1241384Notes

Reaction equation

HRID 1241384 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH:3]=1.[H-].[Na+].Cl[C:25]1[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=1>>[N:8]1([C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:1][C:25]3[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=3)[CH:3]=2)[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934608Tert-butyl 4-(6-aminopyrimidin-4-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 219346512-(6-(1,4-Diazepan-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

Procedure

Tert-butyl 4-(6-aminopyrimidin-4-yl)-1,4-diazepane-1-carboxylate 15-2 (0.50 g, 1.70 mmol), sodium hydride (0.136 g, 3.4 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.246 g, 1.70 mmol) were treated as in Scheme 4 above. The product was purified on a C18 preparative column after treating the crude product with trifluoroacetic acid and then isolated via lyophilization. Hi-Res MS: calc: 302.1182 found: 302.1184. 1NMR (CD3OD): 8.45 ppm (s, 1H); 8.01 ppm (s, 1H); 6.16 ppm (s, 1H); 4.08 ppm (m, 2H); 3.73 ppm (m, 2H); 3.40 ppm (m, 2H); 3.32 ppm (m, 2H); 2.21 ppm (m, 2H).

Workup

  1. customThe product was purified on a C18 preparative column
  2. additionafter treating the crude product with trifluoroacetic acid
  3. customisolated via lyophilization

Sources & evidence

ORD record
ord-9f9628b6f5664effb0b9babfcb481047
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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