HCID 11778364, compound → HCID 11579568, compound

HRID 1991466Notes

Reaction equation

HRID 1991466 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[C:16]2[C:15]([C:17](OCC)=[O:18])=[CH:14][C:13]([CH3:22])=[N:12][C:11]=2[S:10][C:9]=1[C:23](=[O:25])[NH2:24]>C1COCC1>[NH2:7][C:8]1[C:16]2[C:11](=[N:12][C:13]([CH3:22])=[CH:14][C:15]=2[CH2:17][OH:18])[S:10][C:9]=1[C:23]([NH2:24])=[O:25]

Participants

4

Reactant 2

HCID 11778364HCID 11778364, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11579568HCID 11579568, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (22 g, 0.57 mol) in anhydrous THF (250 mL) was added a solution of ethyl 3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylate (40 g, 143 mmol) in anhydrous THF (250 mL) at −40° C. dropwise. The reaction was then allowed to warm to room temperature and the mixture was heated to reflux and stirred for 5 h. After cooling to room temperature, the reaction was quenched by aqueous NaOH (2N, 22 mL) at 0° C., filtered through Celite and washed with THF (50 mL×5). The filtrate was collected and evaporated under reduced pressure to give crude 3-amino-4-hydroxymethyl-6-methyl-thieno[2,3-b]pyridine-2-carboxamide (74%, 25 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter cooling to room temperature
  4. customthe reaction was quenched by aqueous NaOH (2N, 22 mL) at 0° C.
  5. filtrationfiltered through Celite
  6. washwashed with THF (50 mL×5)
  7. customThe filtrate was collected
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a14177501f11481ba98d7573ce8bbc13
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

Loading…