Trifluoroacetic acid → HCID 9903342, compound

HRID 1005720Notes

Reaction equation

HRID 1005720 reaction equation
COC1C=C(C=CC=1OC)C[NH:7][C:8]1[N:9]=[C:10]([C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[O:18])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=1.C(O)(C(F)(F)F)=O>>[NH2:7][C:8]1[N:9]=[C:10]([C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[O:18])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22674465HCID 22674465, compound

Product 1

HCID 9903342HCID 9903342, compoundYield 102%

Procedure

A mixture of 2-[N-(3,4-dimethoxybenzyl)]aminothieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.06 g, 0.15 mmol) and TFA (2 mL) was refluxed for 2 h, cooled, concentrated in vacuo to half its original volume, diluted with CH2Cl2 (50 mL), washed with saturated sodium bicarbonate solution (3×25 mL) then brine (25 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; heptane-EtOAc (3:1)] to give the title compound (40 mg, 100%) as a yellow solid.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo to half its original volume
  4. additiondiluted with CH2Cl2 (50 mL)
  5. washwashed with saturated sodium bicarbonate solution (3×25 mL)
  6. dry with materialbrine (25 mL), dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by chromatography [SiO2; heptane-EtOAc (3:1)]

Sources & evidence

ORD record
ord-c1d03f538a324faf9ba9ec0065de95b9
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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