Potassium Carbonate → HCID 68509812, compound

HRID 2241242Notes

Reaction equation

HRID 2241242 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16](Cl)=[C:11]3[C:10]([CH3:18])=[N:9]2)=[CH:5][CH:4]=1.[CH:21]1([CH2:24][NH:25][C:26]2[N:31]([CH3:32])[C:30](=[O:33])[C:29]([C:34]3[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([F:41])[CH:35]=3)=[CH:28][N:27]=2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].CC([O-])(C)C.[K+]>CN(C=O)C>[CH:21]1([CH2:24][NH:25][C:26]2[N:31]([CH3:32])[C:30](=[O:33])[C:29]([C:34]3[CH:39]=[CH:38][C:37]([O:40][C:16]4[CH:15]=[CH:14][N:13]=[C:12]5[N:8]([CH2:7][C:6]6[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][CH:5]=6)[N:9]=[C:10]([CH3:18])[C:11]=45)=[C:36]([F:41])[CH:35]=3)=[CH:28][N:27]=2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 23665647Potassium tert-butoxideHCID 685123991-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridineHCID 68518200HCID 68518200, compound

Product 1

HCID 68509812HCID 68509812, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a 15 mL capacity reaction tube were added 1-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine (20 mg, 0.07 mmol; prepared according to the procedure of Example 43, Step E) and 2-(cyclopropylmethylamino)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one (22.1 mg, 0.077 mmol) and the solids were dissolved in DMF (1 mL) under nitrogen. Potassium carbonate (10.6 mg, 0.0765 mmol) was added, followed by KOtBu (0.077 mL, 0.077 mmol, 1M solution in THF). The reaction tube was sealed and the reaction mixture was stirred at 110° C. for 1 hour. The reaction mixture was partitioned between water (5 mL) and ethyl acetate (10 mL). The organic layer was separated and the aqueous layer was extracted with a second portion of ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl, dried over sodium sulfate and evaporated to afford 37.5 mg of a red semi-solid. The crude product was purified by silica gel chromatography (Biotage 12M) eluting with 2% MeOH/DCM to afford a red colored glass (23.8 mg, 63%). LRMS (APCI pos) m/e 541.3 (M+1).

Workup

  1. customTo a 15 mL capacity reaction tube
  2. customprepared
  3. customThe reaction tube was sealed
  4. customThe reaction mixture was partitioned between water (5 mL) and ethyl acetate (10 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with a second portion of ethyl acetate
  7. washThe combined organic layers were washed with saturated aqueous NaCl
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-104aac4f2c8c4e25a034570960eb6807
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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