Triethylamine → HCID 22011937, compound

HRID 1532957Notes

Reaction equation

HRID 1532957 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]([CH3:17])[CH2:13]1.CC1CC(O)CO1.C(N(CC)CC)C>O>[Cl:8][C:7]1[C:2]([NH:11][CH:12]2[CH2:16][O:15][CH:14]([CH3:17])[CH2:13]2)=[N:3][CH:4]=[N:5][C:6]=1[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 347412,5-Anhydro-1,3-dideoxypentitolHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 22011941Pentitol,2-amino-1,4-anhydro-2,3,5-trideoxy-(9CI)

Product 1

HCID 22011937HCID 22011937, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

1.5 g of 4,5-dichloro-6-ethylpyrimidine (8.5 mmol), 0.86 g (8.5 mmol) of 4-amino-2-methyltetrahydrofuran (prepared from 2-methyltetrahydrofuran4-ol analogously to the route given for Example A) and 2 ml (14 mmol) of triethylamine were heated for 6 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 (8:2, 7:3). This gave 1.73 g (84% of theory) of a colorless oil (diastereomers 2:1).

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-ebbd76da17b9409793fced008f75a2ea
Source dataset
uspto-grants-2001_03
Patent number
US06207668B1

Reaction notes

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