Isopropanol → HCID 86723850, compound

HRID 576751Notes

Reaction equation

HRID 576751 reaction equation
[I:1][C:2]1[C:3](=[O:20])[NH:4][C:5](=[O:19])[N:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[CH3:18])[CH:7]=1.[CH:21](O)([CH3:23])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[I:1][C:2]1[C:3](=[O:20])[N:4]([CH:21]([CH3:23])[CH3:22])[C:5](=[O:19])[N:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[CH3:18])[CH:7]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86723851HCID 86723851, compound

Product 1

HCID 86723850HCID 86723850, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-iodo-1-(2-methyl-5-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 118) (645 mg) in THF (20 ml) were added isopropyl alcohol (0.25 ml), triphenylphosphine (855 mg), diethyl azodicarboxylate (2.2 M toluene solution, 1.48 ml), and the resulting mixture was stirred at room temperature for twenty-five minutes. The reaction solutions were concentrated under reduced pressure and the residue was then purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 5-iodo-3-isopropyl-1-(2-methyl-5-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (548 mg).

Workup

  1. concentrationThe reaction solutions were concentrated under reduced pressure
  2. customthe residue was then purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-05b7db69acc3442a981c312ccfaf6a76
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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