Formic Acid → HCID 11529219, compound

HRID 536088Notes

Reaction equation

HRID 536088 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][N:8]2[C:13]3[CH:14]=[CH:15][NH:16][C:12]=3[C:11](=[O:17])[NH:10][C:9]2=[S:18])[CH2:2]1.[CH:19](O)=O.[BH3-]C#N.[Na+]>CO>[CH3:19][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][N:8]2[C:13]3[CH:14]=[CH:15][NH:16][C:12]=3[C:11](=[O:17])[NH:10][C:9]2=[S:18])[CH2:2]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 5003444Sodium cyanoborohydrideHCID 11708736HCID 11708736, compound

Product 1

HCID 11529219HCID 11529219, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Piperidin-3-ylmethyl-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one (Example 7) (0.092 g, 0.35 mmol) was dissolved in methanol (2 mL) and formic acid (37% aq., 0.059 mL, 0.7 mmol) was added. After 5 minutes of stirring at r.t. a precipitate had formed. NaCNBH3 (0.026 g, 0.42 mmol) was added and the mixture was stirred at r.t. for 1 h. The solvent was removed in vacuo and the residual solid was purified by preparative HPLC, obtaining the title compound (0.022 g, 22%) as a white solid.

Workup

  1. customhad formed
  2. stirringthe mixture was stirred at r.t. for 1 h
  3. customThe solvent was removed in vacuo
  4. customthe residual solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-5866f4f36ec6497f98f0762ef611eaa7
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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