Dichloromethane → HCID 178441720, compound

HRID 1182818Notes

Reaction equation

HRID 1182818 reaction equation
ClCCl.[NH:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]3[C:23](=[O:47])[N:24]([C:33]4[N:38]=[CH:37][C:36]([O:39][CH:40]5[CH2:45][CH2:44][CH:43]([OH:46])[CH2:42][CH2:41]5)=[CH:35][N:34]=4)[C:25]([CH3:32])=[N:26][C:27]=3[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:17][CH:16]=2)=[N:7][N:6]=[N:5]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O>[NH:7]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]3[C:23](=[O:47])[N:24]([C:33]4[N:38]=[CH:37][C:36]([O:39][CH:40]5[CH2:41][CH2:42][C:43](=[O:46])[CH2:44][CH2:45]5)=[CH:35][N:34]=4)[C:25]([CH3:32])=[N:26][C:27]=3[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:17][CH:16]=2)=[N:4][N:5]=[N:6]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087Triacetoxyperiodinane2×HCID 178441721HCID 178441721, compound

Product 1

HCID 178441720HCID 178441720, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the dichloromethane (0.5 mL) solution of 5-{[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-6-butyl-3-[5-(4-hydroxycyclohexyloxy)pyrimidin-2-yl]-2-methylpyrimidin-4 (3H)-one (10 mg, 0.017 mmol), Dess-Martin reagent (11 mg, 0.026 mmol) was added and stirred at room temperature for 1 hr. Dess-Martin reagent (11 mg, 0.026 mmol) was added, and further stirred at room temperature overnight. The reaction mixture was added water and extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (chloroform:methanol=5:1) to obtain the target compound.

Workup

  1. stirringfurther stirred at room temperature overnight
  2. extractionextracted with chloroform
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain the target compound

Sources & evidence

ORD record
ord-b897448ddc054c518c82300fd1a807d5
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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