Tetrahydrofuran → Diisopropylethylamine

HRID 1838193Notes

Reaction equation

HRID 1838193 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[N:5]=[C:4]([S:23][CH3:24])[N:3]=1.[F:25][C:26]([F:30])([F:29])[CH2:27][O-:28].O1[CH2:35][CH2:34][CH2:33]C1>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:6]3[C:7]([C:8]#[N:9])=[C:2]([O:28][CH2:27][C:26]([F:30])([F:29])[F:25])[N:3]=[C:4]([S:23][CH3:24])[N:5]=3)[CH2:11][CH2:12]2)=[CH:17][CH:18]=1.[CH2:15]([N:10]([CH:11]([CH3:12])[CH3:26])[CH:34]([CH3:35])[CH3:33])[CH3:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 144719362,2,2-TrifluoroethanolateHCID 187532704-Chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile

Product 2

HCID 81531DiisopropylethylamineHCID 187532314-[4-(4-Fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile

Procedure

In analogy to the procedure described in example 59b, 4-chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile (example 57a) was treated with 2,2,2-trifluoroethanolate in tetrahydrofurane at room temperature during 18 hours to yield the 4-phenyl-piperidine in the presence of N-ethyl-diisopropylamine at room temperature during 18 hours to yield 4-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile as an amorphous, yellow solid; MS: [M+H]+=427.

Sources & evidence

ORD record
ord-2ef13b07a47446b68e2a292be9b4d41c
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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