Sodium hydride → 5-Octyl-2-(4-(5,5-difluoro-5-(perfluorobutoxyethoxy) pentoxy)phenyl)pyrimidine

HRID 374736Notes

Reaction equation

HRID 374736 reaction equation
[H-].[Na+].[CH2:3]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H][H].C1(C)C(S(O[CH2:36][CH2:37][CH2:38][CH2:39][C:40]([F:63])([F:62])[O:41][C:42]([F:61])([F:60])[C:43]([F:59])([F:58])[O:44][C:45]([F:57])([F:56])[C:46]([F:55])([F:54])[C:47]([F:53])([F:52])[C:48]([F:51])([F:50])[F:49])(=O)=O)=CC=CC=1>CN(C)C=O>[CH2:3]([C:11]1[CH:16]=[N:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([F:62])([F:63])[O:41][C:42]([F:60])([F:61])[C:43]([F:58])([F:59])[O:44][C:45]([F:57])([F:56])[C:46]([F:54])([F:55])[C:47]([F:52])([F:53])[C:48]([F:49])([F:51])[F:50])=[CH:19][CH:18]=2)=[N:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 1317192385,5-Difluoro-5-(perfluorobutoxyethoxy)-1-pentanol toluenesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 212253305-Octyl-2-(4-(5,5-difluoro-5-(perfluorobutoxyethoxy) pentoxy)phenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Using essentially the procedure of Example 97, a flask was charged with sodium hydride (0.4 g of a 60 weight % suspension in mineral oil, 1.65 mmoles) and dimethyl formamide (5 mL). With stirring, 5-octyl-2-(4-hydroxyphenyl)pyrimidine (0.33 g, 1.1 mmole) was slowly added to the resulting mixture to control the hydrogen evolution. The mixture was stirred at room temperature for 30 minutes, 5,5-difluoro-5-(perfluorobutoxyethoxy)-1-pentanol toluenesulfonate (0.6 g, 0.95 mmoles) was then added, and the mixture was heated at 100° C. for one hour. The mixture was worked up essentially as in Example 99 and was distilled using a Kugelrohr apparatus (b.p. approximately 180°-200° C. at 0.4 torr). The product yield was 5.72 g (structure confirmed by 1H and 19F nuclear magnetic resonance spectroscopy).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. distillationwas distilled

Sources & evidence

ORD record
ord-33301f1f9e924610bc4439d0bc960ad5
Source dataset
uspto-grants-1996_01
Patent number
US05482650

Reaction notes

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