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

HRID 1241379Notes

Reaction equation

HRID 1241379 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH:3]=1.[H-].[Na+].Cl[C:24]1[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=1>>[N:8]1([C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:1][C:24]3[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=3)[CH:3]=2)[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934614tert-Butyl 4-(6-aminopyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 219346302-(6-(Piperazin-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

Procedure

Tert-butyl 4-(6-aminopyrimidin-4-yl)piperazine-1-carboxylate 12-2 (0.25 g, 0.9 mmol), sodium hydride (0.072 g, 1.8 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.129 g, 0.9 mmol) were treated as in Scheme 4 above. The product was purified on a C18 preparative column and evaporated to dryness. The residue was then treated with trifluoroacetic acid and the product was isolated from a sodium carbonate/methyene chloride partition. 1H-NMR (CD3OD): 8.47 ppm (s, 1H); 8.02 ppm (s, 1H); 6.24 ppm (s, 1H); 3.88 ppm (t, 4H); 3.27 ppm (t, 4H).

Workup

  1. customThe product was purified on a C18 preparative column
  2. customevaporated to dryness
  3. additionThe residue was then treated with trifluoroacetic acid

Sources & evidence

ORD record
ord-a8dd6b32a8ad48519e43abeb09cef542
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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