Ammonium formate → HCID 178522800, compound

HRID 574662Notes

Reaction equation

HRID 574662 reaction equation
[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:32])=[N:19][C:20]([CH2:23][O:24]CC2C=CC=CC=2)=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:32])=[N:19][C:20]([CH2:23][OH:24])=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178522799N-benzhydryl-2-(benzyloxymethyl)-4-hydroxypyrimidine-5-carboxamide2×

Product 1

HCID 178522800HCID 178522800, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of step E product, 2-f, (3.0 g, 7 mmol), ammonium formate (0.9 g, 14 mmol) and Pd/C (0.6 g) in MeOH (70 mL) was refluxed overnight. The reaction solution was filtered. The filtrate was evaporated under vacuum to obtain a residue, which was purified by silica gel chromatography by eluting with PE:EA=1:2 and DCM:MeOH=10:1 to afford the product, 2-g, (0.51 g, 21%). 1H NMR (300 MHz, CDCl3): δ4.47 (s, 2H), 6.30-6.32 (d, Hz, 1H), 7.23-7.25 (m, 11H), 8.72 (s, 1H), 9.98-10.00 (s, 1H).

Workup

  1. filtrationThe reaction solution was filtered
  2. customThe filtrate was evaporated under vacuum
  3. customto obtain a residue, which
  4. customwas purified by silica gel chromatography
  5. washby eluting with PE

Sources & evidence

ORD record
ord-3870b3f3c2ed49b68341be4b9c563be1
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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