Ethyl Acetate → 4-[2-(4-Methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

HRID 861110

Reaction equation

HRID 861110 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:8]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[N:9][N:10]2[C:15]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:14][CH:13]=[CH:12][C:11]=12)=O.S(O)(O)(=O)=O.[NH2:35][C:36]([NH2:38])=[NH:37].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:8]2[C:7]([C:5]3[CH:4]=[CH:3][N:35]=[C:36]([NH2:38])[N:37]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[N:10]3[N:9]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 499987Guanidine Sulfate (1:1)HCID 57494731(2E)-3-(dimethylamino)-1-[2-(4-methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propen-1-one

Product 1

HCID 574447144-[2-(4-Methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamineYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2E)-3-(dimethylamino)-1-[2-(4-methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propen-1-one (500 mg, 1.28 mmol) in dimethylformamide (10 mL) was added guanidine sulfate (277 mg, 1.28 mmol), followed by potassium carbonate (195 mg, 1.41 mmol). The resulting solution was heated at reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added. The phases were separated and aqueous phase extracted with additional ethyl acetate. The combined organics were dried (magnesium sulfate), filtered and concentrated in vacuo to give 4-[2-(4-methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (440 mg, 89%) as a yellow solid. 1H NMR (CDCl3): δ 7.98 (d, 1H), 7.80 (d, 1H), 7.56 (dd, 2H), 7.20 (t, 1H), 6.92 (d, 2H), 6.43 (d, 1H), 6.05 (d, 1H), 4.95 (b, 2H), 3.83 (s, 3H), 3.74–3.70 (m, 4H), 2.01–1.98 (m, 4H); MS m/z 387 (M+1).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 6 hours
  3. customThe phases were separated
  4. extractionaqueous phase extracted with additional ethyl acetate
  5. dry with materialThe combined organics were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c04da291309f4552a0af9eab46c76e32
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Linked notes

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