Water → HCID 50906785, compound

HRID 1431330Notes

Reaction equation

HRID 1431330 reaction equation
CO[C:3]1[C:4]2[CH:18]=[CH:17][CH:16]=[N:15][C:5]=2[N:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:8]=1.[O:19]1[CH2:24][CH2:23][N:22]([C:25]2[C:30]([NH2:31])=[CH:29][C:28]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:27][N:26]=2)[CH2:21][CH2:20]1.[H-].[Na+].O>CN(C)C=O>[N:22]1([C:25]2[C:30]([NH:31][C:3]3[C:4]4[CH:18]=[CH:17][CH:16]=[N:15][C:5]=4[N:6]=[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=4)[N:8]=3)=[CH:29][C:28]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[CH:27][N:26]=2)[CH2:21][CH2:20][O:19][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 596310462,5-Dimorpholinopyridin-3-amineHCID 59631553HCID 59631553, compound

Product 1

HCID 50906785HCID 50906785, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-methoxy-2-(pyridin-2-yl)pyrido[2,3-d]pyrimidine (0.050 g, 0.21 mmol) and 2,5-dimorpholinopyridin-3-amine (0.061 g, 0.23 mmol) in N,N-dimethylformamide (2.0 mL) was added 60% sodium hydride (9.23 mg, 0.23 mmol). The reaction was heated to 60° C. Stirring continued overnight. The reaction was cooled to rt and water was added to quench. The reaction was extracted with EtOAc (3×10 mL). The combined organic layer were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0 to 30% MeOH in DCM) to give N-(2,5-di-4-morpholinyl-3-pyridinyl)-2-(2-pyridinyl)pyrido[2,3-d]pyrimidin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 9.75 (1H, d, J=2.7 Hz), 9.36 (1H, br. s.), 9.23 (1H, dd, J=4.4, 1.7 Hz), 8.87 (1H, d, J=8.0 Hz), 8.70 (1H, m), 8.30 (1H, dd, J=8.2, 1.8 Hz), 7.91 (1H, m), 7.84 (1H, d, J=2.7 Hz), 7.62 (1H, dd, J=8.2, 4.3 Hz), 7.42-7.49 (1H, m), 3.94-4.04 (8H, m), 3.43-3.55 (4H, br m), 3.09 (4H, br. m.). Mass Spectrum (ESI) m/e=471.3 (M+1).

Workup

  1. temperatureThe reaction was cooled to rt
  2. customto quench
  3. extractionThe reaction was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic layer were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (0 to 30% MeOH in DCM)

Sources & evidence

ORD record
ord-a5d5eea420ef4c32b4e95108eae994e9
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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