Water → HCID 15346448, compound

HRID 651408Notes

Reaction equation

HRID 651408 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].[CH3:16][C:17](=O)[CH2:18][CH2:19][CH2:20][CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:18]([C:17]1([CH3:16])[O:15][CH2:14][CH:11]([NH:10][C:3]2[C:2]([Cl:1])=[C:7]([CH2:8][CH3:9])[N:6]=[CH:5][N:4]=2)[CH2:12][O:13]1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 115832-HexanoneHCID 15346449HCID 15346449, compound

Product 1

HCID 15346448HCID 15346448, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.16 g (9 mmol) of 5-chloro-6-ethyl-4-(1,3-dihydroxy-2-propylamino)-pyrimidine (Example 1), 1.80 g (18 mmol) of 2-hexanone and 500 mg of p-toluenesulfonic acid were heated in 100 ml of toluene for 8 hours, using a water separator. After the mixture had been extracted by stirring with dilute sodium hydroxide solution, the organic phase was dried and concentrated. The cis/trans isomers were separated by chromatography over silica gel (mobile phase: ethyl acetate/petroleum ether 4:1). 0.29 g of trans isomer (10.3% of theory, colorless oil) was first eluted, followed by 0.49 g of the cis isomer (17.3% of theory, colorless oil).

Workup

  1. extractionAfter the mixture had been extracted
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. customThe cis/trans isomers were separated by chromatography over silica gel (mobile phase: ethyl acetate/petroleum ether 4:1)

Sources & evidence

ORD record
ord-20d327168a5148fa970a3ff03c3fbf7d
Source dataset
uspto-grants-2001_08
Patent number
US06281221B1

Reaction notes

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