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 129011노트

반응식

HRID 129011 반응식
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

참가 물질

8

반응물 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

생성물 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-one수율 90%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-218727b6fe7e4875878e95f9a3b1ecb4
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466692

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