1-Octanol → 2-(3-Benzyloxyphenyl)-5-octyloxypyrimidine

HRID 2399199Notes

Reaction equation

HRID 2399199 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH2:32]([O:39][C:40]1[CH:41]=[C:42]([C:46]2[N:51]=[CH:50][C:49]([OH:52])=[CH:48][N:47]=2)[CH:43]=[CH:44][CH:45]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[CH2:53](O)[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]>O1CCCC1>[CH2:32]([O:39][C:40]1[CH:41]=[C:42]([C:46]2[N:47]=[CH:48][C:49]([O:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[CH:50][N:51]=2)[CH:43]=[CH:44][CH:45]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 193862292-(3-Benzyloxyphenyl)-5-hydroxypyrimidine

Product 1

HCID 193862272-(3-Benzyloxyphenyl)-5-octyloxypyrimidineYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.52 g (21.05 mmol) of triphenylphosphine and 3.67 g (21.05 mmol) of diethyl azodicarboxylate are stirred at 0° C. for 30 minutes in 100 ml of tetrahydrofuran. 3.90 g (14.03 mmol) of 2-(3-benzyloxyphenyl)-5-hydroxypyrimidine and 2.74 g (21.05 mmol) of 1-octanol are subsequently added, and the resultant solution is stirred at room temperature for 18 hours. Evaporation to dryness and purification by chromatography (silica gel/dichloromethane) give 4.25 g of 2-(3-benzyloxyphenyl)-5-octyloxypyrimidine. ##STR29## Removal of the benzyl protecting group by hydrogenation analogously to Example 1 gives 2-(3-hydroxyphenyl)-5-octyloxypyrimidine. ##STR30## 2-(3-Hydroxyphenyl)-5-octyloxypyrimidine is reacted with methanol analogously to Example 1 to give 2-(3-methoxyphenyl)-5-octyloxypyrimidine. ##STR31## The compound has the phase sequence: X43 I

Workup

  1. customEvaporation
  2. customto dryness and purification by chromatography (silica gel/dichloromethane)

Sources & evidence

ORD record
ord-7a5439b0ad524e329cb1fa0f10f61c73
Source dataset
uspto-grants-1995_09
Patent number
US05447656

Reaction notes

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