Ammonium Hydroxide → HCID 86666564, compound

HRID 2088871Notes

Reaction equation

HRID 2088871 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH2:14][CH3:15])[CH2:9][C:10](OC)=[O:11])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[OH-].[NH4+:18]>O>[Cl:1][C:2]1[C:7]2[C@H:8]([CH2:14][CH3:15])[CH2:9][C:10](=[O:11])[NH:18][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86666565HCID 86666565, compound

Product 1

HCID 86666564HCID 86666564, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

Dissolve methyl 3-(4,6-dichloropyrimidin-5-yl)pentanoate (10.00 g, 38.01 mmol) in 28% ammonium hydroxide in water (95 mL) and seal in a 350 mL tube. Heat the reaction mixture to 200° C. for 2 hours. Cool the reaction mixture in an ice bath, then filter and wash with cold water. Dry the solids under vacuum to give the racemate. Chiral separation (Chiralpak AS-H, 100% ethanol w/0.2% dimethyl ethylamine) provides the title compound as enantiomer 2 (3.19 g, 40%) (>99% ee). MS (ES) m/z=212 [M]+.

Workup

  1. customseal in a 350 mL tube
  2. temperatureCool the reaction mixture in an ice bath
  3. filtrationfilter
  4. washwash with cold water
  5. customDry the solids under vacuum
  6. customto give the racemate
  7. customChiral separation (Chiralpak AS-H, 100% ethanol w/0.2% dimethyl ethylamine)

Sources & evidence

ORD record
ord-f446f15438bf4f19856e443b81a58ddd
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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