Sodium hydride → HCID 21934707, compound

HRID 1241382Notes

Reaction equation

HRID 1241382 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:12][CH2:11][CH:10]([NH:13]C(=O)OC(C)(C)C)[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>>[NH2:13][CH:10]1[CH2:11][CH2:12][N:8]([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]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934621HCID 21934621, compound

Product 1

HCID 21934707HCID 21934707, compound

Procedure

Tert-butyl 1-(6-aminopyrimidin-4-yl)pyrrolidin-3-ylcarbamate 14-2 (0.483 g, 1.73 mmol), sodium hydride (0.277 g, 6.92 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.25 g, 1.73 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: 288.1026 found: 288.1046. 1NMR (CD3OD): 8.43 ppm (s, 1H); 8.0 ppm (s, 1H); 6.02 ppm (s, 1H); 4.05 ppm (m, 1H); 3.87 ppm (m, 1H); 3.69 ppm (m, 3H); 2.51 ppm (m, 1H); 2.22 ppm (m, 1H).

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-ee5d212bca0a439ab041c73a5b37f7d3
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…