3-Chlorophenol → HCID 131735713, compound

HRID 2200753Notes

Reaction equation

Br[C:2]1[N:10]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[N:7]([CH2:17][CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:6](=[O:28])[N:5]([CH3:29])[C:4]=2[N:3]=1.[Cl:30][C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Si:21]([O:20][CH2:19][CH2:18][CH2:17][N:7]1[C:8](=[O:16])[C:9]2[N:10]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]([O:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([Cl:30])[CH:32]=3)=[N:3][C:4]=2[N:5]([CH3:29])[C:6]1=[O:28])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

Step 1 8-Bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-isopentyl-3-methyl-1H-purine-2,6(3H,7H)-dione (0.50 g, 1.03 mmol, intermediate 82), 3-chlorophenol (0.14 g, 1.08 mmol), potassium carbonate (0.29 g, 2.06 mmol) were combined in DMF (5 mL) and heated at 90° C. for 15 h. The reaction was cooled, diluted with water (100 mL) and extracted with ethyl acetate (3×75 mL). The combined extracts were washed with 1 N LiCl (2×75 mL), dried with magnesium sulfate, filtered and evaporated under reduced pressure to give 1-(3-((tert-butyldimethylsilyl)oxy)propyl-8-(3-chlorophenoxy)-7-isopentyl-3-methyl-1H-purine-2,6(3H,7H)-dione (0.55 g, 100% yield) as a yellow oil. LCMS retention time=6.238 min and 85% purity, LCMS MH+=535.

Workup

temperatureThe reaction was cooled
extractionextracted with ethyl acetate (3×75 mL)
washThe combined extracts were washed with 1 N LiCl (2×75 mL)
dry with materialdried with magnesium sulfate
filtrationfiltered
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-6b8a4e1da4b94f0dbf5c73d1f5d7f094
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

Loading…