Methanol → 7-[5-[(4-Fluorophenyl)methyl]oxazol-2-yl]-6-hydroxy-1-[2-oxo-2-(1-piperidyl)ethyl]imidazo[1,2-a]pyrimidin-5-one

HRID 1971820Notes

Reaction equation

HRID 1971820 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][N:18]([CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:12]2=[N:11][C:10]=1[C:28]1[O:29][C:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[CH:31][N:32]=1)C1C=CC=CC=1.[Si](I)(C)(C)C.CO.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C>[F:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][C:30]2[O:29][C:28]([C:10]3[N:11]=[C:12]4[N:18]([CH2:19][C:20](=[O:27])[N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]5)[CH:17]=[CH:16][N:13]4[C:14](=[O:15])[C:9]=3[OH:8])=[N:32][CH:31]=2)=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 58126861HCID 58126861, compound

Product 1

HCID 1362109187-[5-[(4-Fluorophenyl)methyl]oxazol-2-yl]-6-hydroxy-1-[2-oxo-2-(1-piperidyl)ethyl]imidazo[1,2-a]pyrimidin-5-oneYield 24.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of example 6 (50 mg, 0.092 mmol) in acetonitrile (2 ml) was added TMSI (150 mg, 0.75 mmol) drop-wise at room temperature. The mixture was stirred for 8 hours, after which methanol (0.1 ml) was added to quench the reaction. Then saturated solution of Na2S2O3 was added drop-wise till a yellow solid was precipitated. The resulting solids were collected by filtration, washed with ethyl acetate to give the desired product (10 mg, 24% yield).

Workup

  1. customto quench
  2. customthe reaction
  3. customwas precipitated
  4. filtrationThe resulting solids were collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-e9bc79689afd4b75bdc1f3bfcc6034f4
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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