Formamide → HCID 178518068, compound

HRID 2369401Notes

Reaction equation

HRID 2369401 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:6]=1[C:7]([O:9]CC)=O.[CH:18]([NH2:20])=O>>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:5]1[C:6]2[C:7]([OH:9])=[N:20][CH:18]=[N:1][C:2]=2[S:3][CH:4]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 16784966HCID 16784966, compound

Product 1

HCID 178518068HCID 178518068, compound

Conditions

Temperature
180 °C

Procedure

A 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was charged with ethyl 2-amino-4-(pyridin-2-yl)thiophene-3-carboxylate (10 g, 40.27 mmol, 1.00 equiv) and formamide (100 mL). The resulting solution was stirred for 4 h at 180° C. The reaction mixture was cooled to 20° C. with a water/ice bath. The reaction was then quenched by the addition of 200 mL of water. The resulting solution was extracted with 5×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×100 mL of brine. The organic layers combined was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/methanol (30:1-10:1). Purification resulted in 4 g (43%) of 5-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-ol as a yellow solid. MS: m/z 249 (M+H)+.

Workup

  1. customA 250-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe reaction mixture was cooled to 20° C. with a water/ice bath
  4. customThe reaction was then quenched by the addition of 200 mL of water
  5. extractionThe resulting solution was extracted with 5×100 mL of ethyl acetate
  6. washThe resulting mixture was washed with 1×100 mL of brine
  7. dry with materialThe organic layers combined was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customPurification
  10. customresulted in 4 g (43%) of 5-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-ol as a yellow solid

Sources & evidence

ORD record
ord-ab2584424b264eccb971db54d22715ed
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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