Tetrahydrofuran → HCID 68514108, compound

HRID 2241228Notes

Reaction equation

HRID 2241228 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:20][O:21][C:22]1[CH:39]=[CH:38][C:25]([CH2:26][N:27]2[C:31]3=[N:32][CH:33]=[CH:34][C:35](Cl)=[C:30]3[C:29]([CH3:37])=[N:28]2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][C:35]1[CH:34]=[CH:33][N:32]=[C:31]2[N:27]([CH2:26][C:25]3[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:39][CH:38]=3)[N:28]=[C:29]([CH3:37])[C:30]=12

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 23665647Potassium tert-butoxideHCID 68512367HCID 68512367, compoundHCID 685123991-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 68514108HCID 68514108, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a round bottom flask were added 3-(3-fluoro-4-hydroxyphenyl)-3,4-dihydroquinazolin-2(1H)-one (19 mg, 0.074 mmol) and DMF (0.7 mL). 1-(4-Methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine (25.4 mg, 0.088 mmol), prepared according to the procedure of Example 43, Step E, was added followed by potassium carbonate (12.2 mg, 0.088 mmol) and a 1 M solution of potassium t-butoxide in THF (0.088 mL, 0.088 mmol). The mixture was stirred at 110° C. for 4 hours under nitrogen. The reaction was cooled to room temperature and the reaction mixture was partitioned between water (10 mL) and ethyl acetate (20 mL). The organic layer was separated and the aqueous layer was extracted with a second portion of ethyl acetate (10 mL). The combined organic layers were washed with brine, dried over sodium sulfate and evaporated to give 29.8 mg of brown oil. The crude oil was triturated with a dichloromethane:ether mixture and the resulting solid was filtered and dried to afford the desired product as a tan solid (17.6 mg, 47%). LRMS (APCI pos): m/e 510.2 (M+1).

Workup

  1. additionwas added
  2. temperatureThe reaction was cooled to room temperature
  3. customthe reaction mixture was partitioned between water (10 mL) and ethyl acetate (20 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with a second portion of ethyl acetate (10 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-a955b59b228e4431be31a9111f35429c
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…