Triethyl phosphite → HCID 53781352, compound

HRID 1274607Notes

Reaction equation

HRID 1274607 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.[P:25]([O:32]CC)([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28].C(OCC)C.C(Cl)Cl>C(OCC)C.O1CCCC1>[CH2:27]([O:26][P:25]([CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1)(=[O:32])[O:29][CH2:30][CH3:31])[CH3:28]

Participants

6

Reactant 3

HCID 31215Triethyl phosphiteHCID 21881112Ethyl ether methylene chlorideHCID 22119928HCID 22119928, compound

Product 1

HCID 53781352HCID 53781352, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.00 g, 0.00240 mol) in diethyl ether is cooled to 10° C., treated dropwise with triethyl phosphite (0.580 mL, 0.00340 mol), stirred at 10° C. for 90 minutes, diluted with 10 mL of tetrahydrofuran, stirred at room temperature overnight, refluxed for 1 day, cooled, partially concentrated in vacuo and diluted with methylene chloride. The resultant organic solution is washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow solid. Flash column chromatography of the solid using silica gel and a diethyl ether/methylene chloride solution (1:1) gives the title product as a white solid (0.930 g, mp 142-144° C.).

Workup

  1. stirringstirred at room temperature overnight
  2. temperaturerefluxed for 1 day
  3. temperaturecooled
  4. concentrationpartially concentrated in vacuo
  5. additiondiluted with methylene chloride
  6. washThe resultant organic solution is washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto obtain a yellow solid

Sources & evidence

ORD record
ord-671ee889cf594ff9b3b8a5de0d61f311
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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