Potassium Hydroxide → HCID 60123482, compound

HRID 2416420Notes

Reaction equation

HRID 2416420 reaction equation
C([O:4][C@H:5]([CH3:26])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([NH:22][CH3:23])=[CH:18][C:19]([CH3:21])=[N:20][C:13]=2[N:12]([CH3:24])[C:11]1=[O:25])(=O)C.[OH-].[K+]>O.CO>[CH3:24][N:12]1[C:13]2[N:20]=[C:19]([CH3:21])[CH:18]=[C:17]([NH:22][CH3:23])[C:14]=2[C:15](=[O:16])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:26])[C:11]1=[O:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69732790HCID 69732790, compound

Product 1

HCID 60123482HCID 60123482, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To the crude (R)-3-(5-acetoxyhexyl)-1,7-dimethyl-5-(N-methylamino)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione was added a solution of potassium hydroxide (100 mg) in 20% water-methanol (2 ml). After stirring at room temperature for 1 hour, the mixture was concentrated under reduced pressure to remove methanol. The aqueous mixture was extracted with ethyl acetate (10 ml). The extract was dried over sodium sulfate and the residue was purified by short column chromatography eluting with ethyl acetate to provide (R)-1,7-dimethyl-3-(5-hydroxyhexyl)-5-(N-methylamino)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione 15 mg, 76% yield for 2 steps) as an oil. 1H NMR (300 MHz, benzene d6) δ 0.98 (d, 3H), 1.25-1.50 (m, 4H), 1.70-1.82 (m, 2H), 2.18 (d, 3H), 2.27 (s, 3H), 3.49-3.58 (m, 1H), 3.60 (s, 3H), 4.11 (t, 2H), 5.70 (s, 1H), 9.09 (broad s, 1H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto remove methanol
  3. extractionThe aqueous mixture was extracted with ethyl acetate (10 ml)
  4. dry with materialThe extract was dried over sodium sulfate
  5. customthe residue was purified by short column chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-9e11609e6c354b2e8c4db2b28f8c4259
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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