Triethylamine → HCID 22011939, compound

HRID 1532954Notes

Reaction equation

HRID 1532954 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.[NH2:11][CH:12]1[CH2:16][O:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13]1.C(N(CC)CC)C>O>[Cl:8][C:7]1[C:2]([NH:11][CH:12]2[CH2:16][O:15][CH:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[N:3][CH:4]=[N:5][C:6]=1[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 22011938HCID 22011938, compound

Product 1

HCID 22011939HCID 22011939, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.50 g (8.5 mmol) of 4,5-dichloro-6-ethylpyrimidine, 1.39 g (8.5 mmol) of 4-amino-2-phenyltetrahydrofuran and 2 ml (14 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 the mixture had been dried and concentrated, the residue was purified by column chromatography using petroleum etherlethyl acetate (9:1, 8:2). This gave 1.63 g (63% of theory) of a colorless oil (diastereomers 1:1).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washthe organic phase was washed with saturated NaCl solution
  4. customAfter the mixture had been dried
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d34792147bef4462a54114a73ac56575
Source dataset
uspto-grants-2001_03
Patent number
US06207668B1

Reaction notes

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