2-(4-Trifluoromethylphenyl)-5-pent-1-ynylpyrimidine → 2-(4-Trifluoromethylphenyl)-5-pentylpyrimidine

HRID 1603307Notes

Reaction equation

HRID 1603307 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH3:19])=[CH:11][N:10]=2)=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:13][N:14]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 540644602-(4-Trifluoromethylphenyl)-5-pent-1-ynylpyrimidine

Product 1

HCID 139315742-(4-Trifluoromethylphenyl)-5-pentylpyrimidineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

--The pentynylphenylpyrimidine 40 (1.00 g, 3.45 mmol) was hydrogenated over 5% Pd/C in ethyl acetate to give the arylpentylpyrimidine 41 (0.96 g, 95%) (from MeOH/H2O), transitions/° C. K 51.0 (SA 42.1) 1; νmax /cm-1 (KBr) 2930, 2860, 1545, 1430, 1315s, 1165, 1140, 1070 and 1015, δ 0.91 (3H, t, Me), 1.37 (4H, m), 1.69 (2H, quint, ArCH2CH2), 2.66 (2H, t, ArCH2), 7.75 (2H, d, 3'- and 5'-H), 8.54(2H, d, 2'- and 6'-H) and 8.66 (2H, s, 4- and 6-H); m/z 294 (M+), 275, 251, 237 (M+ -C4H9), 224, 210 and 172.

Sources & evidence

ORD record
ord-7d31b07d64064a6da41a3af3878f0d5b
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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