1-Butoxy-4-chlorobutane → 5-(4-Butoxybutoxy)-2-[4-(5-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentoxy)phenyl)pyrimidine

HRID 582999Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][C:22]([O:25][C:26]([F:39])([F:38])[C:27]([F:37])([F:36])[O:28][C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])([F:24])[F:23])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:40]([O:44][CH2:45][CH2:46][CH2:47][CH2:48]Cl)[CH2:41][CH2:42][CH3:43]>>[CH2:40]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][O:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][C:22]([O:25][C:26]([F:39])([F:38])[C:27]([F:36])([F:37])[O:28][C:29]([F:34])([F:35])[C:30]([F:31])([F:32])[F:33])([F:24])[F:23])=[CH:12][CH:13]=2)=[N:4][CH:3]=1)[CH2:41][CH2:42][CH3:43]

Participants

Reactant 2

HCID 137481391-Butoxy-4-chlorobutane

HCID 21225360HCID 21225360, compound

Product 1

HCID 867543055-(4-Butoxybutoxy)-2-[4-(5-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentoxy)phenyl)pyrimidine

Procedure

The title compound was prepared essentially as in Example 12 by combining 5-hydroxy-2-[4-(5-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentoxy)phenyl]pyrimidine (3.0 g, 5.1 mmol) with 4-butoxybutyl chloride (1.0 g, 6.1 mmol). The reaction mixture was quenched with water, and the crude product was further purified by recrystallization from ethanol, followed by Kugelrohr distillation (230-40° C. at 0.5 torr), to provide a yield of 2.4 g.

Workup

customThe reaction mixture was quenched with water
customthe crude product was further purified by recrystallization from ethanol
distillationfollowed by Kugelrohr distillation (230-40° C. at 0.5 torr)
customto provide a yield of 2.4 g

Sources & evidence

ORD record: ord-8bae760cb70f464db5e3757882b7a0cb
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05928562

Reaction notes

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