2-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine → 2-[2,3-Difluoro-4-(octyloxy)phenyl]-5-nonylpyrimidine

HRID 1603305Notes

Reaction equation

HRID 1603305 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:18]1[N:23]=[CH:22][C:21]([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:20][N:19]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:18]1[N:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:22][N:23]=1

Participants

4

Reactant 1

HCID 544551022-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine

Product 1

HCID 149934662-[2,3-Difluoro-4-(octyloxy)phenyl]-5-nonylpyrimidineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

--The nonynylpyrimidine 38 (1.50 g, 3.39 mmol) was hydrogenated over 5% Pd/C in ethyl acetate to give the nonylpyrimidine 39 (1.39 g, 92%) (from MeOH/EtOH), transitions/° C. K 42.8 SC 53.6 I; νmax /cm-1 (KBr) 2920, 2950, 1625, 1540, 1475, 1465, 1430, 1310, 1200 and 1080s; δ 0.90(6H, m, Me×2), 1.16-1.56 (22H, m), 1.67 (2H, quint, ArCH2CH2), 1.85 (2H, quint, OCH2CH2), 2.63 (2H, t, ArCH2), 4.10 (2H, t, OCH2), 6.82 (1H, ddd, J8.5, 8 and 2, 5'-H), 7.80 (1H, ddd, J8.5, 8 and 2, 6'-H) and 8.65 (2H, s, 4- and 6-H); m/z 446 (M+), 334, 305, 277, 263, 249, 235 and 222.

Sources & evidence

ORD record
ord-ea08fce2cede4fad860dbc7cb94f0664
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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