HCID 9903342, compound → HCID 22674402, compound

HRID 1005725Notes

Reaction equation

HRID 1005725 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[O:12])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.Cl.[CH3:19][N:20]([CH3:25])[CH2:21][C:22]([Cl:24])=[O:23]>N1C=CC=CC=1>[ClH:24].[CH3:19][N:20]([CH3:25])[CH2:21][C:22]([NH:1][C:2]1[N:3]=[C:4]([C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[O:12])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1)=[O:23]

Participants

4

Reactant 2

HCID 9903342HCID 9903342, compoundHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride

Product 1

HCID 22674402HCID 22674402, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-aminothieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.15 g, 0.57 mmol) in anhydrous pyridine (6 mL) under argon at 0° C. was treated with N,N-dimethylglycinyl chloride hydrochloride (0.11 g, 0.69 mmol), warmed to room temperature, refluxed for 16 h, cooled, concentrated in vacuo and partitioned between 3-M HCl (25 mL) and EtOAc (25 mL). The aqueous phase was washed with EtOAc (25 mL), filtered through celite, basified to pH 12 with 10% aqueous sodium hydroxide and the resulting precipitate filtered and dried in vacuo to give a brown solid which was purified by chromatography [SiO2; EtOAc-MeOH (100:0 to 85:15)]. The resulting yellow solid was dissolved in CH2Cl2 (5 mL), treated with 1-M HCl in ether (0.25 mL) and the resulting precipitate filtered and dried in vacuo to give the title compound (32 mg, 11%) as a yellow solid.

Workup

  1. temperaturerefluxed for 16 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. custompartitioned between 3-M HCl (25 mL) and EtOAc (25 mL)
  5. washThe aqueous phase was washed with EtOAc (25 mL)
  6. filtrationfiltered through celite
  7. filtrationthe resulting precipitate filtered
  8. customdried in vacuo
  9. customto give a brown solid which
  10. customwas purified by chromatography [SiO2; EtOAc-MeOH (100:0 to 85:15)]
  11. dissolutionThe resulting yellow solid was dissolved in CH2Cl2 (5 mL)
  12. additiontreated with 1-M HCl in ether (0.25 mL)
  13. filtrationthe resulting precipitate filtered
  14. customdried in vacuo

Sources & evidence

ORD record
ord-a145af1a0dc3494780d59ab0a8ca6a62
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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