Sodium hydride → 2-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile

HRID 1241404Notes

Reaction equation

HRID 1241404 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[H-].[Na+].Cl[C:12]1[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=1>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 2380124-Amino-6-chloropyrimidineHCID 14852222-Chlorothiazole-5-carbonitrile

Product 1

HCID 116873242-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-2 (2.0 g, 15.4 mmol) and 1 equivalent of sodium hydride (0.62 g, 15.4 mmol) were suspended in THF and stirred for 20 minutes before adding 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (2.23 g, 15.4 mmol) and the other equivalent sodium hydride simultaneously. The reaction was refluxed for 1.5 hours, cooled, quenched with methanol and water, evaporated to dryness and partitioned between methylene chloride, methanol and water. The aqueous layer was evaporated to dryness and purified on a silica column (DCM to 9:1:0.1 DCM:MeOH:NH4OH) to afford 35-1. 1H-NMR (CD3OD): 8.75(s, 1H); 8.10(s, 1H); 7.09(s, 1H).

Workup

  1. temperatureThe reaction was refluxed for 1.5 hours
  2. temperaturecooled
  3. customquenched with methanol and water
  4. customevaporated to dryness
  5. custompartitioned between methylene chloride, methanol and water
  6. customThe aqueous layer was evaporated to dryness
  7. custompurified on a silica column (DCM to 9:1:0.1 DCM:MeOH:NH4OH)
  8. customto afford 35-1

Sources & evidence

ORD record
ord-e8b771499dad44a6b480d89bf0ac6c8a
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…