Lithium iodide → 2-(4-(Benzo[d]thiazol-6-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid

HRID 1399682Notes

Reaction equation

HRID 1399682 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3[C:15]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19]C)=[O:18])=[C:14]([CH3:24])[N:13]=[C:12]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[I-].[Li+]>N1C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3[C:15]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([OH:19])=[O:18])=[C:14]([CH3:24])[N:13]=[C:12]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 50997145Methyl 2-(4-(benzo[d]thiazol-6-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 509973242-(4-(Benzo[d]thiazol-6-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acidYield 37.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
125 °C

Procedure

Methyl 2-(4-(benzo[d]thiazol-6-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.041 g; 0.098 mmol) and lithium iodide (0.039 mg; 0.295 mmol) were placed in a microwave vial and dissolved in pyridine (0.7 mL). The vial was purged with nitrogen and heated to 125° C. for 48 h. The solvent was removed under reduced pressure, the residue was dissolved in water and the pH of the solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N until a precipitate formed. The precipitate was collected by filtration and dried under reduced pressure over phosphorus pentoxide. Purification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane furnished 0.015 g (35%) of the title compound as a brown solid.

Workup

  1. customThe vial was purged with nitrogen
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. additionthe pH of the solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N until a precipitate
  5. customformed
  6. filtrationThe precipitate was collected by filtration
  7. dry with materialdried under reduced pressure over phosphorus pentoxide
  8. customPurification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane

Sources & evidence

ORD record
ord-2184c178b0d8419db57b6d55e998106a
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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