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 489245ノート

反応式

HRID 489245 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-815acfc269f844319814f72b415834a0
出典データセット
uspto-grants-2005_12
特許番号
US06977267B2

反応ノート

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