Potassium Carbonate → HCID 90403261, compound

HRID 2200550Notes

Reaction equation

HRID 2200550 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][OH:15])[C:6](=[O:16])[N:5]([CH3:17])[C:4]=2[N:3]=1.Cl[CH2:19][C:20]1[S:21][C:22]([CH3:25])=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Br:1][C:2]1[N:10]([CH2:19][C:20]2[S:21][C:22]([CH3:25])=[CH:23][N:24]=2)[C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][OH:15])[C:6](=[O:16])[N:5]([CH3:17])[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 205558492-(Chloromethyl)-5-methyl-1,3-thiazole hydrochloride2×HCID 90402404HCID 90402404, compound

Product 1

HCID 90403261HCID 90403261, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 8-bromo-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.5 g, 1.65 mmol) in DMF (50 mL) was added 2-(chloromethyl)-5-methylthiazole (0.27 g, 1.81 mmol, intermediate 4), potassium carbonate (0.34 g, 2.48 mmol) and TBAI (2 mg, 0.02 mmol). The mixture was heated at 60° C. for 3 h. The mixture was cooled; then partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was purified by a column chromatography eluting with DCM/methanol (60:1 to 30:1) to give 8-bromo-1-(3-hydroxypropyl)-3-methyl-7-((5-methylthiazol-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione (0.4 g, 58.4%) as a yellow oil which was used without further purification. LCMS MH+ 416.

Workup

  1. temperatureThe mixture was cooled
  2. customthen partitioned between ethyl acetate and water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by a column chromatography
  7. washeluting with DCM/methanol (60:1 to 30:1)

Sources & evidence

ORD record
ord-11bfea2db7c4464693b16119c46874c4
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…