3-Fluorophenol → HCID 46913677, compound

HRID 925572Notes

Reaction equation

HRID 925572 reaction equation
Cl[C:2]1[N:3]([CH2:18][CH2:19][CH3:20])[C:4](=[O:17])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[N:8][C:9]=2[N:10]=1.CN1CCCC1=O.C(=O)([O-])[O-].[K+].[K+].[F:34][C:35]1[CH:36]=[C:37]([OH:41])[CH:38]=[CH:39][CH:40]=1>O>[F:34][C:35]1[CH:36]=[C:37]([CH:38]=[CH:39][CH:40]=1)[O:41][C:2]1[N:3]([CH2:18][CH2:19][CH3:20])[C:4](=[O:17])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[N:8][C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 46913776HCID 46913776, compound

Product 1

HCID 46913677HCID 46913677, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
87.5 °C

Procedure

The first two steps were carried out as described earlier. A mixture of 2-Chloro-8-(1-methyl-1H-pyrazol-4-yl)-1-propyl-1,7-dihydro-purin-6-one (0.1 g, 0.34 mmol), N-methyl pyrrolidone (2 ml), potassium carbonate (0.093 g, 0.68 mmol) and 3-Fluoro phenol (0.036 ml, 0.4 mmol), were heated at 85-90° C. for 20 hours. The reaction mixture was cooled to 0° C. and then added water (10 ml). The solid obtained was filtered, washed with cold water, then washed with diethyl ether, dried to obtain -(3-Fluoro-phenoxy)-8-(1-methyl-1H-pyrazol-4-yl)-1-propyl-1,7dihydro-purin-6-one (0.093 g, 75%) as an off white solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customThe solid obtained
  3. filtrationwas filtered
  4. washwashed with cold water
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-2c610e1fbedd4ccf9d6fe2dca15b8298
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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