2-Aminothiazole → HCID 21934641, compound

HRID 1241431Notes

Reaction equation

HRID 1241431 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].[H-].[Na+].[Cl:9][C:10]1[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=1>C1COCC1>[Cl:9][C:10]1[N:11]=[CH:12][N:13]=[C:14]([NH:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 24758Sodium hydride2×HCID 709434,6-Dichloropyrimidine

Product 1

HCID 21934641HCID 21934641, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3-Thiazol-2-amine 52-1 (2.0 g, 20.0 mmol) was dissolved in THF and 1 equivalent of sodium hydride (0.8 g, 60% dispersion in oil) was added. This was stirred for 30 min at room temperature. Then 4,6-dichloropyrimidine 7-1 (2.97 g, 20.0 mmol) and the other equivalent of sodium hydride were added simultaneously. This was refluxed for 30 minutes. The reaction was quenched with methanol and water and then evaporated. The residue was partitioned with DCM:MeOH:water (50:5:50). The organic layer was drawn off, dried and evaporated to afford crude material which was purified on a silica column eluted with 99:1:0.1 (DCM:MeOH:NH4OH). Rf=0.4 (DCM:MeOH:NH4OH 98:2:0.2). 1H-NMR(DMSO-d6): 11.96 (s, 1H); 8.71(s, 1H); 7.49(d, 1H); 7.25(d, 1H); 7.13(br s, 1H).

Workup

  1. temperatureThis was refluxed for 30 minutes
  2. customThe reaction was quenched with methanol and water
  3. customevaporated
  4. customThe residue was partitioned with DCM:MeOH:water (50:5:50)
  5. customdried
  6. customevaporated
  7. customto afford crude material which
  8. customwas purified on a silica column
  9. washeluted with 99:1:0.1 (DCM:MeOH:NH4OH)

Sources & evidence

ORD record
ord-1acf65b2f2124209bb989cba748dc27c
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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