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

HRID 1603306Notes

Reaction equation

HRID 1603306 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12](Br)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[CH:18]#[C:19][CH2:20][CH2:21][CH3:22].FC1C(F)=C(OCCCCCCCC)C=CC=1C1N=CC(C#CCCCCCCC)=CN=1.[K+].[Br-]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C(NC(C)C)(C)C>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([C:18]#[C:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 123091-PentyneHCID 253877Potassium BromideHCID 232970515-Bromo-2-(4-trifluoromethylphenyl)pyrimidineHCID 544551022-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine

Product 1

HCID 540644602-(4-Trifluoromethylphenyl)-5-pent-1-ynylpyrimidineYield 86.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 7912DiisopropylamineSolvent

Procedure

--Quantities: 2-[4'-Trifluoromethylphenyl]-5-bromopyrimidine 10 (1.48 g, 4.88 mmol), pent-1-yne (0.96 ml, 9.76 mmol), tetrakis(triphenylphosphine)palladium (350 mg, 0.30 mmol), copper(I) iodide (57 mg, 0.30 mmol), diisopropylamine (20 ml). The experimental procedure was as described for compound 38 to give the pentynylpyrimidine 40 (1.22 g, 86%) (from MeOH), m.p. 140.5° C., νmax /cm-1 (KBr) 2970, 2200(C≡C), 1520, 1430, 1325s, 1165, 1115, 1075 and 1015, ≡ 1.07(3H, t, Me), 1.68 (2H, sext, CH2CH3), 2.47 (2H, t, CH2C≡C), 7.74 (2H, d, 3'- and 5'-H), 8.55(2H, d, 2' and 6'-H) and 8.79 (2H, s, 4- and 6-H); m/z 290 (M+), 275, 261, 248, 172 and 152.

Sources & evidence

ORD record
ord-e838e35061a040d09d61a8f3b5732be4
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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