1-Pentyne → 2-(4'-Fluorophenyl)-5-pent-1-ynylpyrimidine

HRID 1603308

반응식

HRID 1603308 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11](Br)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH:15]#[C:16][CH2:17][CH2:18][CH3:19].FC1C(F)=C(OCCCCCCCC)C=CC=1C1N=CC(C#CCCCCCCC)=CN=1>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]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:15]#[C:16][CH2:17][CH2:18][CH3:19])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 123091-PentyneHCID 232970645-Bromo-2-(4-fluorophenyl)pyrimidineHCID 544551022-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine

생성물 1

HCID 193862632-(4'-Fluorophenyl)-5-pent-1-ynylpyrimidine수율 87%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 7912Diisopropylamine용매

실험 절차

--Quantities: 2-(4'-fluorophenyl)-5-bromo-pyrimidine 20 (1.48 g, 4.88 mmol), pent-1-yne (0.98 ml, 10 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. The crude product was purified by flash chromatography (8% ethyl acetate-light petroleum) to give the fluorophenylpyrimidine 42 (1.02 g, 85%), m.p. 51° C.; νmax /cm-1 (KBr) 2960, 2870, 2220, 1600, 1510, 1430, 1220, 1150 and 855; δ 1.07 (3H, t, Me), 1.68 (2H, sext, CH2CH3), 2.47 (2H, t, CH2C≡C), 7.18 (2H, t, 3'- and 5'-H), 8.44 (2H, dd, 2'- and 6'-H) and 8.75 (2H, s, 4- and 6-H); m/z 240 (M+), 225, 212, 198, 184, 171 and 118.

후처리

  1. customThe crude product was purified by flash chromatography (8% ethyl acetate-light petroleum)

출처 및 근거

ORD 기록
ord-ed1bb7e6f9554ff6afd79009163be1ae
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986096

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