Iodomethyl pivalate → HCID 19811547, compound

HRID 373235Notes

Reaction equation

HRID 373235 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].[C:34]([O:40][CH2:41]I)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:34]([O:40][CH2:41][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)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 178458743HCID 178458743, compound

Product 1

HCID 19811547HCID 19811547, compoundYield 81%

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), pivaloyloxymethyl iodide (90 mg) and sodium bicarbonate (35 mg) in DMF (2 ml) was stirred at room temperature for 20 hours. The reaction mixture was evaporated to dryness and the residue was dissolved in chloroform-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 (0.1 g, 81%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in chloroform-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-6fa409d914ed4b3bbdfb5fd3156a4aca
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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