Methanol → 2-(3-Methoxyphenyl)-5-(4-octyloxyphenyl)pyrimidine

HRID 2399195Notes

Reaction equation

HRID 2399195 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:22]=[C:23]([C:27]2[N:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:35][CH:34]=3)=[CH:29][N:28]=2)[CH:24]=[CH:25][CH:26]=1.CO>O1CCCC1>[CH3:1][O:20][C:21]1[CH:22]=[C:23]([C:27]2[N:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:35][CH:34]=3)=[CH:29][N:28]=2)[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 19386210HCID 19386210, compound

Product 1

HCID 193862222-(3-Methoxyphenyl)-5-(4-octyloxyphenyl)pyrimidineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.50 g (5.76 mmol) of triphenylphosphine and 0.90 ml (5.76 mmol) of diethyl azodicarboxylste in 40 ml of tetrahydrofuran are stirred at 0° C. for 30 minutes. 1.50 g (3.84 mmol) of 2-(3-hydroxyphenyl)-5-(4-octyloxyphenyl)pyrimidine and 0.23 ml (5.76 mmol) of methanol are subsequently added, and the resultant solution is stirred at room temperature overnight. Evaporation to dryness, chromatographic purification (silica gel/dichloromethane:ethyl acetate=95:5) and recrystallization from acetonitrile give 1.20 g of 2-(3-methoxyphenyl)-5-(4-octyloxyphenyl)pyrimidine. ##STR16##

Workup

  1. customEvaporation
  2. customto dryness, chromatographic purification (silica gel/dichloromethane:ethyl acetate=95:5) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-e8aea7d635594076a2d27475597f3fb3
Source dataset
uspto-grants-1995_09
Patent number
US05447656

Reaction notes

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