Methyl iodide → HCID 19811538, compound

HRID 373234Notes

Reaction equation

HRID 373234 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH3:14])[N:6]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:5]1=[O:33])[CH2:2][CH3:3].CI.[C:36](=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:36][N:29]1[C:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:19]2[CH:20]=[CH:21][C:16]([CH2:15][N:6]3[C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:8][C:9](=[O:10])[N:4]([CH2:1][CH2:2][CH3:3])[C:5]3=[O:33])=[CH:17][CH:18]=2)=[N:32][N:31]=[N:30]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 178458743HCID 178458743, compound

Product 1

HCID 19811538HCID 19811538, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-propyl-6-propyloxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.1 g), methyl iodide (50 mg) and sodium bicarbonate (25 mg) in DMF (5 ml) was stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness and the residue was dissolved in CHCl3 -water. The chloroform layer was dried and evaporated in vacuo to give a syrup. The syrup was column-chromatographed on silica gel to give a colorless syrup (90 mg, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in CHCl3 -water
  3. dry with materialThe chloroform layer was dried
  4. customevaporated in vacuo
  5. customto give a syrup
  6. customThe syrup was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-1b6f885fee0a4f6fb3a81fe9b305ae4d
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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