Carbon tetrabromide → 3'-[7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile

HRID 478236

反応式

HRID 478236 の反応式
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[N:4]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Na].[NH:51]1[CH:55]=[N:54][CH:53]=[N:52]1>ClCCl>[N:51]1([CH2:2][C:3]2[CH:8]=[CH:7][N:6]3[C:9]([C:12]4[CH:13]=[C:14]([C:18]5[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH:15]=[CH:16][CH:17]=4)=[CH:10][N:11]=[C:5]3[N:4]=2)[CH:55]=[N:54][CH:53]=[N:52]1

参加物

6

反応物 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 180012733'-(7-Hydroxymethylimidazo[1,2-a]pyrimidin-3-yl)-biphenyl-2-carbonitrileHCID 454898221h-1,2,4-Triazole sodium salt

生成物 1

HCID 101564263'-[7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile収率 13.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3′-(7-hydroxymethylimidazo[1,2-a]pyrimidin-3-yl)-biphenyl-2-carbonitrile (0.1 g, 0.31 mmol) in dichloromethane (5 ml) was added carbon tetrabromide (153 mg, 0.46 mmol) and triphenylphosphine (121 mg, 0.46 mmol). This mixture was stirred at ambient temperature for 6 h after which time 1,2,4-triazole sodium salt (84 mg, 0.93 mmol) was added and the reaction stirred at ambient temperature for a further 18 h. The solvent was removed in vacuo and the residue purified by silica gel chromatography eluting with dichloromethane on a gradient of methanol (0-10%). Further purification by high performance liquid chromatography gave 3′-[7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile (15.3 mg): δH (400 MHz, DMSO) 5.76 (2H, s), 7.32 (1H, d, J 7), 7.52-7.84 (8H, m), 8.16 (2H, d, J 5), 8.73 (1H, s), 9.22 (1H, s); m/z (ES+) 378 (M++H).

後処理

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by silica gel chromatography
  4. washeluting with dichloromethane on a gradient of methanol (0-10%)
  5. customFurther purification by high performance liquid chromatography

出典と根拠

ORDレコード
ord-5fa89201e1514e85b78c5c438c17d266
出典データセット
uspto-grants-2003_11
特許番号
US06642229B2

関連ノート

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