Potassium Hydroxide → HCID 60123481, compound

HRID 2416422Notes

Reaction equation

HRID 2416422 reaction equation
C([O:4][C@H:5]([CH3:27])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([N:22]([CH3:24])[CH3:23])=[CH:18][C:19]([CH3:21])=[N:20][C:13]=2[N:12]([CH3:25])[C:11]1=[O:26])(=O)C.[OH-].[K+]>O.CO>[CH3:25][N:12]1[C:13]2[N:20]=[C:19]([CH3:21])[CH:18]=[C:17]([N:22]([CH3:24])[CH3:23])[C:14]=2[C:15](=[O:16])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:27])[C:11]1=[O:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69732926HCID 69732926, compound

Product 1

HCID 60123481HCID 60123481, compoundYield 79%

Reagents, catalysts & solvents 1

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

Procedure

To crude (R)-3-(5-acetoxyhexyl)-1,7-dimethyl-5-(N,N-dimethylamino)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione was added a solution of potassium hydroxide (100 mg) in 10% water-methanol (2.2 ml). After stirring at room temperature for 2 hours, the mixture was concentrated under reduced pressure. The residue was treated with saturated aqueous sodium chloride solution (10 ml) and ethyl acetate (10 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford (R)-1,7-dimethyl-5-(N,N-dimethylamino)-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (55 mg, 79% yield for 2 steps) as an oil. 1H NMR (300 MHz, benzene d6) δ 1.13 (d, 3H), 1.20-1.50 (m, 4H), 1.56-1.72 (m, 2H), 2.11 (s, 3H), 3.40 (s, 3H), 3.55 (m, 1H), 3.90 (t, 2H), 6.21 (s, 1H), 7.15 (s, 1H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was treated with saturated aqueous sodium chloride solution (10 ml) and ethyl acetate (10 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-24e76f4c4fbb4d1abb1d0b5637cdd89a
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

Loading…