Acetonitrile → 5-Benzyloxy-2-[4-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

HRID 582963Notes

Reaction equation

C([C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:12][CH:13]=1)C1C=CC=CC=1.[F:21][C:22]([F:50])([C:46]([F:49])([F:48])[F:47])[C:23]([F:45])([F:44])[C:24]([F:43])([F:42])[O:25][C:26]([F:41])([F:40])[C:27]([F:39])([F:38])[O:28][C:29]([F:37])([F:36])[CH2:30][O:31][CH2:32][CH2:33][CH2:34]Br.[C:51](=[O:54])([O-])[O-].[K+].[K+].[C:57](#N)[CH3:58]>O>[CH2:51]([O:54][C:8]1[CH:13]=[N:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:34][CH2:33][CH2:32][O:31][CH2:30][C:29]([O:28][C:27]([F:39])([F:38])[C:26]([F:41])([F:40])[O:25][C:24]([F:43])([F:42])[C:23]([F:45])([F:44])[C:22]([F:50])([F:21])[C:46]([F:49])([F:48])[F:47])([F:37])[F:36])=[CH:18][CH:19]=2)=[N:10][CH:9]=1)[C:58]1[CH:57]=[CH:16][CH:15]=[CH:14][CH:11]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A 500 mL flask was charged with 5-benzyl-2-[4-hydroxyphenyl]pyrimidine (10.0 g, 40 mmol), 3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromopropane (24.2 g, 44 mmol, Example 3), potassium carbonate (6.1 g, 44 mmol), and anhydrous acetonitrile (100 mL), and the resulting mixture was stirred overnight at 85° C. under nitrogen. Water (150 mL) was added and the mixture was cooled to 5° C. and then filtered and dried to produce 5-benzyloxy-2-[4-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine. This intermediate was further purified by recrystallization from acetone, and the benzyl protecting group was removed by hydrogenation using Pd/C catalyst.

Workup

temperaturethe mixture was cooled to 5° C.
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-263aa2072c584bb590dc3dd66b26d491
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05928562

Reaction notes

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