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Ammonium formate → (S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

HRID 633759
Notes
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Reaction equation

HRID 633759 reaction equation
C([O-])=O.[NH4+].C([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]2[C:25]3=[N:26][C:27]([N:31]4[CH2:37][CH:36]5[O:38][CH:33]([CH2:34][CH2:35]5)[CH2:32]4)=[CH:28][C:29](=[O:30])[N:24]3[CH2:23][C@@:22]2([CH3:43])[C:39]([F:42])([F:41])[F:40])=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]2[C:25]3=[N:26][C:27]([N:31]4[CH2:32][CH:33]5[O:38][CH:36]([CH2:35][CH2:34]5)[CH2:37]4)=[CH:28][C:29](=[O:30])[N:24]3[CH2:23][C@@:22]2([CH3:43])[C:39]([F:42])([F:41])[F:40])=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 118194495(S)-1-[2-(4-benzyloxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 72709217(S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 2

HCID 9942167
Palladium hydroxide
Catalyst
HCID 887MethanolSolvent

Procedure

700 mg (11.10 mmol) of ammonium formate and 156 mg (0.22 mmol) of 20% palladium hydroxide are added at 0° C. to a solution of 1.20 g (2.22 mmol) of (S)-1-[2-(4-benzyloxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one in 15 mL of methanol. The mixture is refluxed for 1 hour and then allowed to cool to room temperature. The reaction medium is filtered through Celite and the filtrate is then evaporated to dryness. After purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 25 min 10% B, t 30 min 10% B), 732 mg of (S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one were obtained, corresponding to the following characteristics:

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. filtrationThe reaction medium is filtered through Celite
  3. customthe filtrate is then evaporated to dryness
  4. customAfter purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 25 min 10% B, t 30 min 10% B), 732 mg of (S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one
  5. customwere obtained, corresponding to the following characteristics

Sources & evidence

ORD record
ord-c245a8dcb4434ed4967f845a31b1c463
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321790B2

Reaction notes

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