Water → HCID 68982099, compound

HRID 1930287Notes

Reaction equation

HRID 1930287 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:21](=[O:22])[N:20]([CH2:23][CH3:24])[C:12]3[N:13]=[C:14](S(C)=O)[N:15]=[CH:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:25][NH2:26].C1COCC1.O>C(Cl)Cl.CCCCCC>[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:21](=[O:22])[N:20]([CH2:23][CH3:24])[C:12]3[N:13]=[C:14]([NH:26][CH3:25])[N:15]=[CH:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 962WaterHCID 66615946Methylamine tetrahydrofuranHCID 69094777HCID 69094777, compound

Product 1

HCID 68982099HCID 68982099, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

Using general method E, 6-(3-amino-4-fluorophenyl)-8-ethyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one from Example 2 (0.94 g, 2.73 mmol) and 2.0M methylamine/THF (2.73 mL, 5.5 mmol) were stirred overnight at RT. Water (50 mL) was added and the product was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford crude product. This crude product was stirred with 60% CH2Cl2/hexane solution (10 mL) for 10 min. The resultant solid was filtered and washed with 60% CH2Cl2/hexane solution and dried to afford 6-(3-amino-4-fluorophenyl)-8-ethyl-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (0.32 g, 37% yield) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 8.62 (s, 1H), 7.82-7.77 (m, 2H), 7.11 (dd, J=8.8 Hz, 1.6 Hz, 1H), 7.00 (dd, J=11.2 Hz, 8.0 Hz, 1H), 6.78-6.74 (m, 1H), 5.14 (s, 2H), 4.39-4.35 (m, 2H), 2.89 (d, J=4.4 Hz, 3H), 1.26-1.22 (m, 3H); MS (ESI) m/z: 314.3 (M+H+).

Workup

  1. extractionthe product was extracted with EtOAc (2×30 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford crude product
  6. filtrationThe resultant solid was filtered
  7. washwashed with 60% CH2Cl2/hexane solution
  8. customdried

Sources & evidence

ORD record
ord-bc9d288580ce431089a75b0d465f195d
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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