5-Trimethylstannyl-pyrimidine → (5S*,9R*)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-9-(4-pyrimidin-5-yl-phenyl)-1,3,7-triazaspiro[4.4]nonane-2,4-dione

HRID 489245노트

반응식

HRID 489245 반응식
[CH2:1]([N:8]1[CH2:27][C@@H:26]([C:28]2[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=2)[C@:10]2([N:14]([CH3:15])[C:13](=[O:16])[N:12]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:11]2=[O:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Sn](C)(C)[C:37]1[CH:38]=[N:39][CH:40]=[N:41][CH:42]=1>C1(C)C=CC=CC=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>[CH2:1]([N:8]1[CH2:27][C@@H:26]([C:28]2[CH:33]=[CH:32][C:31]([C:37]3[CH:38]=[N:39][CH:40]=[N:41][CH:42]=3)=[CH:30][CH:29]=2)[C@:10]2([N:14]([CH3:15])[C:13](=[O:16])[N:12]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:11]2=[O:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 127998215-Trimethylstannyl-pyrimidineHCID 60054841(5S*,9R*)-7-Benzyl-9-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3,7-triazaspiro[4.4]nonane-2,4-dione

생성물 1

HCID 60054825(5S*,9R*)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-9-(4-pyrimidin-5-yl-phenyl)-1,3,7-triazaspiro[4.4]nonane-2,4-dione

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of Example 65 (2 g, 3.58 mmol), 5-trimethylstannyl-pyrimidine (1.3 g, 5.35 mmol, prepared according to patent WO 95/06636) and tetrakis(triphenylphosphine)palladium(0) (620 mg, 0.54 mmol) in toluene (50 ml) was refluxed for 10 h under a nitrogen atmosphere. After cooling to room temperature, the insoluble material was filtered off and washed twice with toluene. The toluene layers were concentrated in vacuo. The resulting orange oil (3.1 g) was chromatographed over silica gel (eluent: EtOAc) to yield the above-titled compound as a white solid after crystallization from MeOH (430 mg), mp=228° C.

후처리

  1. filtrationthe insoluble material was filtered off
  2. washwashed twice with toluene
  3. concentrationThe toluene layers were concentrated in vacuo
  4. customThe resulting orange oil (3.1 g) was chromatographed over silica gel (eluent: EtOAc)

출처 및 근거

ORD 기록
ord-815acfc269f844319814f72b415834a0
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977267B2

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