1-Bromo-3-chloropropane → 5-heptyl-2-[4-(3-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)propoxy)phenyl]pyrimidine

HRID 378205Notes

Reaction equation

HRID 378205 reaction equation
[F:1][C:2]([F:35])([C:31]([F:34])([F:33])[F:32])[C:3]([F:30])([F:29])[C:4]([F:28])([F:27])[O:5][C:6]([F:26])([F:25])[C:7]([F:24])([F:23])[O:8][C:9]([F:22])([F:21])[CH2:10][O:11][CH2:12][C@@H:13]([F:20])[CH2:14][O:15][CH2:16][CH2:17][CH2:18]Cl.FC(F)(C(F)(F)F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)COC[C@@H](F)CO.BrCCCCl.[CH2:72]([C:79]1[CH:80]=[N:81][C:82]([C:85]2[CH:90]=[CH:89][C:88]([OH:91])=[CH:87][CH:86]=2)=[N:83][CH:84]=1)[CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78]>C(#N)C.CN(C)C=O>[CH2:72]([C:79]1[CH:84]=[N:83][C:82]([C:85]2[CH:86]=[CH:87][C:88]([O:91][CH2:18][CH2:17][CH2:16][O:15][CH2:14][C@H:13]([F:20])[CH2:12][O:11][CH2:10][C:9]([O:8][C:7]([F:24])([F:23])[C:6]([F:26])([F:25])[O:5][C:4]([F:28])([F:27])[C:3]([F:30])([F:29])[C:2]([F:35])([F:1])[C:31]([F:34])([F:33])[F:32])([F:22])[F:21])=[CH:89][CH:90]=2)=[N:81][CH:80]=1)[CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78]

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 537730983-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)propyl chlorideHCID 538480713-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropanolHCID 1356171522-(4Hydroxyphenyl)-5-n-heptylpyrimidine

Product 1

HCID 541798415-heptyl-2-[4-(3-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)propoxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

The starting material, 3-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)propyl chloride, was prepared by combining 3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropanol (20 g, 39.4 mmol) and 1-bromo-3-chloropropane (18.6 g, 118 mmol). The resulting compound (2.0 g, 3.4 mmol) was then combined with 5-heptyl-2-(4-hydroxyphenyl)pyrimidine (0.9 g, 3.4 mmol) in acetonitrile/dimethyl formamide (1:1, 20 mL) using essentially the procedure of Example 8 of International Patent Publication No. WO 96/33251. The resulting crude product was further purified by chromatography, eluting with 30:1 toluene/ethyl acetate, followed by Kugelrohr distillation (180-90° C. at 0.01 torr; yield 0.96 g).

Workup

  1. customThe resulting crude product was further purified by chromatography
  2. washeluting with 30:1 toluene/ethyl acetate
  3. distillationfollowed by Kugelrohr distillation (180-90° C. at 0.01 torr; yield 0.96 g)

Sources & evidence

ORD record
ord-641045841bea46c089e02995da3272b1
Source dataset
uspto-grants-2000_02
Patent number
US06030547

Reaction notes

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