Sulfuric Acid → HCID 135983989, compound

HRID 512997Notes

Reaction equation

HRID 512997 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[C:10]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]2[CH3:36])[C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:26]C(C)C)=[C:22]([CH:25]=3)[C:23]#[N:24])=[N:14][C:12]=2[N:13]=1.[OH:37]S(O)(=O)=O.[OH-].[Na+]>O>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[C:10]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]2[CH3:36])[C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([CH:25]=3)[C:23]([NH2:24])=[O:37])=[N:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium Hydroxide2×HCID 57441902HCID 57441902, compound

Product 1

HCID 135983989HCID 135983989, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

5-[2,4-Bis-((S)-3-methyl-morpholin-4-yl)-pyrido[2,3-d]pyrimidin-7-yl]-2-isopropoxy-benzonitrile (1 equiv) was added portionwise to concentrated H2SO4 (0.1 M substrate in acid). The reaction was heated to 90° C. and maintained at this temperature until all starting material had dissolved to give a bright red solution. The mixture was cooled and water (2 reaction volumes) added dropwise, then the solution was neutralized by careful addition of solid NaOH until pH 4-5 was attained. The mixture was cooled and neutralised by addition of 2N NaOH and then extracted using EtOAc (2×10 reaction volumes). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash chromatography (SiO2) using MeOH/DCM—0:100 going to 5:95 as eluent to give the desire product as a yellow powder.

Workup

  1. temperaturemaintained at this temperature until all starting material
  2. dissolutionhad dissolved
  3. customto give a bright red solution
  4. temperatureThe mixture was cooled
  5. temperatureThe mixture was cooled
  6. extractionextracted
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a crude residue which
  11. customwas purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-8b0119b3925946afa44d215d1d9e07ff
Source dataset
uspto-grants-2015_08
Patent number
US09102670B2

Reaction notes

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