Triethylamine → HCID 53734866, compound

HRID 1532959Notes

Reaction equation

HRID 1532959 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.[CH2:11]([N:14]1[CH2:18][CH:17]([NH2:19])[CH2:16][CH:15]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=[CH2:13].C(N1CC(O)CC1C1C=CC=CC=1)C=C.C(N(CC)CC)C>O>[Cl:8][C:7]1[CH:2]=[N:3][C:4]([NH:19][CH:17]2[CH2:18][N:14]([CH2:11][CH:12]=[CH2:13])[CH:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16]2)=[N:5][C:6]=1[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 22011943HCID 22011943, compoundHCID 22011945HCID 22011945, compound

Product 1

HCID 53734866HCID 53734866, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

1.5 g (8.5 mmol) of 4,5-dichloro-6-ethylpyrimidine, 1.7 g (8.5 mmol) of 1-allyl-4-amino-2-phenylpyrrolidine (prepared from 1-allyl-2-phenylpyrrolidin--4-ol analogously to the route described in Example A) and 2 ml (4 mmol) of triethylamine were heated for 12 hours at 85° C. After cooling, the mixture was diluted with water and extracted with ether, and the organic phase was washed with saturated NaCl solution. After drying and concentrating, the residue was purified by column chromatography using petroleum ether/ethyl acetate (9:1, 8:2). This gave 0.95 g (33% of theory) of a colorless syrup (diastereomers 1:1)

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washthe organic phase was washed with saturated NaCl solution
  4. customAfter drying
  5. concentrationconcentrating
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2cbcede352bc4580af5948c5f4013de8
Source dataset
uspto-grants-2001_03
Patent number
US06207668B1

Reaction notes

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