Sodium hydride → HCID 21934704, compound

HRID 1241426Notes

Reaction equation

HRID 1241426 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N: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]=[C:6]([NH:8][C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 3457522-Chloro-4-aminopyrimidineHCID 14852222-Chlorothiazole-5-carbonitrile

Product 1

HCID 21934704HCID 21934704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloropyrimidin-4-amine 49-1 (0.30 g, 2.32 mmol) and sodium hydride (0.093 g, 2.32 mmol) were suspended in dry THF and stirred for 20 minutes before adding 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.33 g, 2.32 mmol) and more sodium hydride (0.093 g, 2.32 mmol) simultaneously. This was refluxed for 1.5 hour and then quenched with methanol and water, and concentrated to dryness. The residue was partitioned between DCM, MeOH, and water. The aqueous layer was evaporated to dryness and then purified on a silica column. 1H-NMR (CD3OD): 8.50(d, 1H); 8.42(s, 1H); 7.11(d, 1H). By 1H-NMR this material is a mixture of the desired product and 2-chloropyrimidin-4-amine in a ratio of 5:8, which was used as is in the next step.

Workup

  1. temperatureThis was refluxed for 1.5 hour
  2. customquenched with methanol and water
  3. concentrationconcentrated to dryness
  4. customThe residue was partitioned between DCM, MeOH, and water
  5. customThe aqueous layer was evaporated to dryness
  6. custompurified on a silica column
  7. additiona mixture of the desired product and 2-chloropyrimidin-4-amine in a ratio of 5:8, which

Sources & evidence

ORD record
ord-4362f0728b624517926e59ac4ea95874
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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