Iodine chloride → HCID 86723847, compound

HRID 576746Notes

Reaction equation

HRID 576746 reaction equation
[OH:1][CH2:2][C@H:3]([N:5]1[C:10](=[O:11])[CH:9]=[CH:8][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:6]1=[O:22])[CH3:4].[I:23]Cl>C(Cl)(Cl)Cl>[OH:1][CH2:2][C@H:3]([N:5]1[C:10](=[O:11])[C:9]([I:23])=[CH:8][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[C:6]1=[O:22])[CH3:4]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 86723846HCID 86723846, compound

Product 1

HCID 86723847HCID 86723847, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (R)-3-(1-hydroxypropan-2-yl)-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 102) (1.3 g) in chloroform (20.0 ml) was added iodine chloride (12.4 ml, 1M dichloromethane solution) and the resulting mixture was stirred for two hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford (R)-3-(1-hydroxypropan-2-yl)-5-iodo-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (1.4 g).

Workup

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

Sources & evidence

ORD record
ord-a4fef27cf4da4e639d009bf9d9802953
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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