Ethanol → 2-Hydroxymethyl-4-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 129011ノート

反応式

HRID 129011 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([CH2:19][OH:20])[N:17]=[CH:18][C:13]=3[CH2:12][CH:11](C)[C:10]2=[O:22])=[CH:4][CH:3]=1.[C:23]([N:27]1[C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2B(O)O)=[N:30][N:29]=[N:28]1)([CH3:26])([CH3:25])[CH3:24].[C:41]([O-])([O-])=O.[Na+].[Na+].CCO>C(Cl)Cl.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.C1(C)C=CC=CC=1>[OH:20][CH2:19][C:16]1[N:17]=[C:18]([CH3:41])[C:13]2[CH2:12][CH2:11][C:10](=[O:22])[N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[C:31]4[N:27]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:28]=[N:29][N:30]=4)=[CH:7][CH:6]=3)[C:14]=2[N:15]=1

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 109447112-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acidHCID 193729978-[(4-bromophenyl)methyl]-2-hydroxymethyl-6-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

生成物 1

HCID 193729942-Hydroxymethyl-4-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one収率 90%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 8-[(4-bromophenyl)methyl]-2-hydroxymethyl-6-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (0.95 g, 2.62 mmol), 2-[(1-tert-butyl)-1H-tetrazol-5-yl]phenylboronic acid (0.72 g, 2.90 mmol) (prepared according to J. W. Ellingboe, et al. U.S. Pat. No. 5,149,699), 2M Na2CO3 (5.5 mL), tetrakis(triphenylphosphine)palladium(0) (100 tug, 0.086 mmol), EtOH (3 mL)and toluene (16 mL) was heated under reflux for 20 h. The mixture was diluted with CH2Cl2 and the layers were separated. The organic phase was dried (MgSO4) and concentrated to give an orange oil. Purification by flash chromatography (4% MeOH/CH2Cl2) gave 1.20 g (90%) of product as a colorless foam.

後処理

  1. customprepared
  2. temperatureunder reflux for 20 h
  3. customthe layers were separated
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give an orange oil
  7. customPurification by flash chromatography (4% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-218727b6fe7e4875878e95f9a3b1ecb4
出典データセット
uspto-grants-1995_11
特許番号
US05466692

反応ノート

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