Tetrahydrofuran → HCID 11579568, compound

HRID 488918Notes

Reaction equation

HRID 488918 reaction equation
[Li+].[BH4-].C([O:5][C:6]([C:8]1[C:9]2[C:17]([NH2:18])=[C:16]([C:19](=[O:21])[NH2:20])[S:15][C:10]=2[N:11]=[C:12]([CH3:14])[CH:13]=1)=O)C.C1COCC1>CO>[NH2:18][C:17]1[C:9]2[C:10](=[N:11][C:12]([CH3:14])=[CH:13][C:8]=2[CH2:6][OH:5])[S:15][C:16]=1[C:19]([NH2:20])=[O:21]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 11778364HCID 11778364, compound

Product 1

HCID 11579568HCID 11579568, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiBH4 (62 mg, 2.04 mmol) was added to a solution of 3-Amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid ethyl ester (205 mg, 0.73 mmol) in 10:1 THF:MeOH (15 mL) at room temperature. After stirring for 2 h, the reaction was quenched by addition of 1M HCl. The mixture was buffered to a pH ≈7, diluted with EtOAc, washed sequentially with H2O, brine, dried over Na2SO4, concentrated, and triturated with 50% EtOAc/hexane giving 3-amino-4-hydroxymethyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide (123 mg, 71%) as a yellow solid, m.p. >210° C.

Workup

  1. customat room temperature
  2. customthe reaction was quenched by addition of 1M HCl
  3. additiondiluted with EtOAc
  4. washwashed sequentially with H2O, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customtriturated with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-7d5bc9a539004b4daf80bfa1ea3b15e9
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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