Tetrahydrofuran → HCID 11579568, compound

HRID 750738Notes

Reaction equation

HRID 750738 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-0a002af586a04227a0fbeb320a6b09f1
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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