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

HRID 1603306
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HRID 1603306 반응식
[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
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

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

실험 절차

--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.

출처 및 근거

ORD 기록
ord-e838e35061a040d09d61a8f3b5732be4
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05986096

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