Triethylamine → HCID 178494686, compound

HRID 1419811Notes

Reaction equation

HRID 1419811 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH2:10][O:11][CH3:12])[N:5]=[CH:4][N:3]=1.[CH3:13][C:14]1([C@@H:20]2[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:9][O:8][C:7]1[C:2]([NH:26][C@H:23]2[CH2:22][CH2:21][C@@H:20]([C:14]3([CH3:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:25][CH2:24]2)=[N:3][CH:4]=[N:5][C:6]=1[CH2:10][O:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152793504-Chloro-5-methoxy-6-(methoxymethyl)pyrimidineHCID 178429769HCID 178429769, compound

Product 1

HCID 178494686HCID 178494686, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.83 g (15 mmol) of 4-chloro-5-methoxy-6-methoxymethylpyrimidine [Collection Czechoslov. Chem. Commun. 33 (1968) 2266], 2.93 g (15 mmol) of cis-4-(1-methylcyclohexyl)cyclohexylamine and 3.03 g (30 mmol) of triethylamine are heated under reflux in 10 ml of toluene for 6 hours. After cooling, the mixture was subjected to extraction by stirring with water, and the organic phase was dried and concentrated. For purification it was chromatographed on silica gel (eluent: ethyl acetate). 1.2 g (23% of theory) of pure cis isomer were obtained as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was subjected to extraction
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. customFor purification it
  6. customwas chromatographed on silica gel (eluent: ethyl acetate)
  7. custom1.2 g (23% of theory) of pure cis isomer were obtained as a colorless oil

Sources & evidence

ORD record
ord-94fa4fffd45b42119960d1c243ce34c5
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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