Ethanol → 4-hydroxymethyl-2-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 129014ノート

反応式

HRID 129014 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]([CH3:21])[N:17]=[C:18]([CH2:19][OH:20])[C:13]=3[CH2:12][CH2:11][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([O-])([O-])=O.[Na+].[Na+].CCO>CCOC(C)=O.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.O>[OH:20][CH2:19][C:18]1[C:13]2[CH2:12][CH2:11][C:10](=[O:22])[N:9]([CH2:8][C:5]3[CH:6]=[CH:7][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:3][CH:4]=3)[C:14]=2[N:15]=[C:16]([CH3:21])[N:17]=1

参加物

9

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 104737918-[(4-Bromophenyl)methyl]4-hydroxymethyl-2-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-oneHCID 109447112-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acid

生成物 1

HCID 193730024-hydroxymethyl-2-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 90.4%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 8-[(4-bromophenyl)methyl]-4-hydroxymethyl-2-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (490 mg, 1.35 mmol), 2-[(1-tert-butyl)-1H-tetrazol-5-yl]phenylboronic acid (367 mg, 1.49 mmol) (prepared according to J. W. Ellingboe, et al. U.S. Pat. No. 5,149,699), Na2CO3 (287 mg, 2.71 mmol), tetrakis(triphenylphosphine)palladium(0) (78 mg, 0.07 mmol), EtOH (1 mL), water (2 mL), and toluene (6 mL) was heated under reflux for 23 h. The mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3, brine, dried (MgSO4), and concentrated to give a yellow oil. Purification by flash chromatography (5% MeOH/CH2Cl2) gave 590 mg (90%) of product as an off-white foam. An analytical sample (40 mg) was crystallized from ether/acetone, mp 164°-166° C.

後処理

  1. customprepared
  2. temperatureunder reflux for 23 h
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by flash chromatography (5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-a3f8c773b8384c2fa4b2b408e25a2b3c
出典データセット
uspto-grants-1995_11
特許番号
US05466692

反応ノート

読み込み中…