Ammonium formate → HCID 136163954, compound

HRID 390349Notes

Reaction equation

HRID 390349 reaction equation
C([O:8][C:9]1(O)[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][CH:10]1[C:22]1[N:23]([CH3:36])[C:24]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[C:25](Cl)[N:26]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[F:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][C:24]2[N:23]([CH3:36])[C:22]([C:10]3[N:11]=[C:12]4[N:17]([C:18](=[O:19])[C:9]=3[OH:8])[CH2:16][CH2:15][O:14][C:13]4([CH3:21])[CH3:20])=[N:26][CH:25]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67434362HCID 67434362, compound

Product 1

HCID 136163954HCID 136163954, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(benzyloxy)-2-(4-chloro-5-(4-fluorobenzyl)-1-methyl-1H-imidazol-2-yl)-3-hydroxy-9,9-dimethyl-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (0.02 g, 0.039 mmol, 1.0 equiv) in EtOH (1 mL) was added ammonium formate (0.04 g, 0.634 mmol, 16 equiv) and 10% Pd/C (0.04 g, 0.376 mmol, 9.6 equiv). After stirring 4 h, LCMS analysis indicated complete conversion to product. The reaction was then filtered through celite and concentrated in vacuo. The crude product was purified by silica gel chromatography (7% MeOH/CH2Cl2) to provide the title compound (0.008 g, 53% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.09-7.19 (m, 2H), 6.97-7.06 (m, J=8.62, 6.48, 2.27 Hz, 2H), 6.90 (s, 1H), 3.99-4.09 (m, 4H), 3.97 (s, 2H), 3.95 (s, 3H), 1.57 (s, 6H); LCMS (ES+, (M+H)+) m/z 385.18.

Workup

  1. filtrationThe reaction was then filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica gel chromatography (7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ba239cca330d4a278add44dbb771cad6
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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