Triethylamine → HCID 57097426, compound

HRID 379535Notes

Reaction equation

HRID 379535 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1CCC(N)CC1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])C.O.Cl[CH2:34]Cl>>[C:11]([O:15][C:16]([N:18]([N:27]1[CH2:28][CH2:29][CH2:34][CH2:31][CH2:30]1)[C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 21908982Water methylene chloride

Product 1

HCID 57097426HCID 57097426, compound

Procedure

17.7 g (0.10 mol) of 4,5-dichloro-6-ethylpyrimidine, 20.0 g 1-(tert-butoxycarbonyl)4-aminopiperidine (0.10 mol) and 15.2 g (0.15 mol) of triethylamine were heated for 8 hours at 80-90°. After cooling, the mixture was worked up with water/dichloromethane and the organic phase was dried and concentrated. For purification, the crude product was chromatographed on silica gel (petroleum ether/ethyl acetate 1:1). This gave 21.7 g (63.6% of theory) of a colorless oil which solidified gradually.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. customFor purification
  5. customthe crude product was chromatographed on silica gel (petroleum ether/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-b9f9b18cde844caca66355b407c7fb9c
Source dataset
uspto-grants-2001_10
Patent number
US06300333B1

Reaction notes

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