5-Chloro-N,N'-bis(3-vinylphenyl)pyrimidine-2,4-diamine Trifluoroacetate → Trifluoroacetate

HRID 541558

반응식

HRID 541558 반응식
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[C:10]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27](C=C)[CH:26]=2)=[N:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[CH2:23])[CH:17]=2)=[N:13][CH:14]=1>ClCCCl.C(#N)C.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[N:13][C:12]2[NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH:17]=3)[CH:22]=[CH:23][C:27]3[CH:26]=[C:25]([NH:24][C:10]=1[N:11]=2)[CH:30]=[CH:29][CH:28]=3.[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4]

참가 물질

6

반응물 1

HCID 668796985-Chloro-N,N'-bis(3-vinylphenyl)pyrimidine-2,4-diamine Trifluoroacetate

생성물 2

HCID 84468Trifluoroacetate수율 66.9%HCID 178478261HCID 178478261, 화합물

시약·촉매·용매 3

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororuthenium촉매HCID 111,2-Dichloroethane용매HCID 6342Acetonitrile용매

반응 조건

온도
130 °C

실험 절차

A solution of 5-chloro-N,N′-bis(3-vinylphenyl)pyrimidine-2,4-diamine trifluoroacetate (21 mg, 0.045 mmol) in 1,2-dichloroethane (20 mL) was degassed by bubbling nitrogen for 5 minutes. Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (11 mg, 0.013 mmol) was added and the mixture was heated to 130° C. for 20 minutes in a microwave. The mixture was evaporated to give a dark mixture which was suspended in acetonitrile and filtered. The filtrate was purified by preparative LCMS (pH 2) to give the desired product as a trifluoroacetate salt (1.7 mg, 9%). LCMS for C18H14ClN4 (M+H)+: m/z=321.1. 1H NMR (400 MHz, CD3Cl): δ 8.85 (s, 1H), 8.75 (s, 1H), 7.90 (s, 1H), 7.55 (s, 1H), 7.25 (m, 3H), 7.02 (m, 4H), 6.60 (s, 2H).

후처리

  1. customby bubbling nitrogen for 5 minutes
  2. customThe mixture was evaporated
  3. customto give a dark mixture which
  4. filtrationfiltered
  5. customThe filtrate was purified by preparative LCMS (pH 2)

출처 및 근거

ORD 기록
ord-7128b85503b74309844d0c1fc7a3dff8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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