Formamide → HCID 178422246, compound

HRID 525087

Reaction equation

HRID 525087 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:12])=[CH:5][C:6]=1[C:7](OCC)=[O:8].[CH:13]([NH2:15])=O>>[CH3:12][C:4]1[S:3][C:2]2[N:1]=[CH:13][N:15]=[C:7]([OH:8])[C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 4062885Ethyl 2-Amino-5-methylthiophene-3-carboxylate

Product 1

HCID 178422246HCID 178422246, compoundYield 25%

Procedure

Into a 25-mL round-bottom flask placed ethyl 2-amino-5-methylthiophene-3-carboxylate (500 mg, 2.70 mmol, 1.00 equiv) in 10 mL of formamide was stirred for 8 h at 180° C. in an oil bath. After completion of the reaction, the reaction mixture was cooled down to room temperature and then quenched with water/ice, extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (2:1) to provide the resulted 6-methylthieno[2,3-d]pyrimidin-4-ol (114 mg, 25%) as a yellow solid. MS (ES, m/z): 167 [M+H+].

Workup

  1. customInto a 25-mL round-bottom flask placed
  2. customAfter completion of the reaction
  3. customquenched with water/ice
  4. extractionextracted with 3×50 mL of ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified on a silica gel column with ethyl acetate/petroleum ether (2:1)

Sources & evidence

ORD record
ord-930bafd7c22541e49b7e9d609d7c21c1
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Linked notes

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