Triethylamine → HCID 15376259, compound

HRID 1532960Notes

Reaction equation

HRID 1532960 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[CH2:17][O:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.C1(C2CCC(O)CO2)C=CC=CC=1.C(N(CC)CC)C>O>[Cl:8][C:7]1[C:2]([NH:11][CH:12]2[CH2:17][O:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[N:3][CH:4]=[N:5][C:6]=1[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 15376258HCID 15376258, compoundHCID 20498269HCID 20498269, compound

Product 1

HCID 15376259HCID 15376259, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

2.4 g (13.5 mmol) of 4,5-dichloro-6-ethylpyrimidine, 2.4 g (13.5 mmol) of 5-amino-2-phenyltetrahydropyran (prepared from 2-phenyltetrahydropyran-5-ol (cf. U.S. Pat. No. 4,388,104) analogously to the routes described in Example A) and 3 ml (21 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 0.65 g (15% of theory) of the trans isomer as a colorless oil and 2.17 g (51% of theory) of the cis isomer as a colorless oil.

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-3d320e174bfa45989fcdd837f478be03
Source dataset
uspto-grants-2001_03
Patent number
US06207668B1

Reaction notes

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