Cesium carbonate → HCID 59173418、化合物

HRID 220096ノート

反応式

HRID 220096 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][CH3:14])[CH:8]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.[C:16]([O:20][C:21](=[O:31])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25](Br)[CH:24]=1)([CH3:19])([CH3:18])[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[CH3:29][C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:21](=[O:31])[O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:28][C:27]=1[NH:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([NH:13][CH3:14])[N:10]=[CH:11][N:12]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58764366tert-Butyl (3-bromo-4-methylphenyl)carbamateHCID 591733071018473-23-8

生成物 1

HCID 59173418HCID 59173418、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a high pressure tube is added 6-(5-amino-3-methyl-1H-pyrazol-1-yl)-N-methylpyrimidin-4-amine 29 (2.0 g, 9.8 mmol), 3-bromo-4-methylphenyl carbamic acid tert-butyl ester 37 (2.4 g, 10.8 mmol), Pd(OAc)2 (132 mg, 0.59 mmol), Cs2CO3 (3.5 g, 10.8 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (340 mg, 0.59 mmol) and 1,4-dioxane (30 mL). The mixture is flushed with N2 at 0° C. for a few minutes, then heated to 120° C. for 2 days. The mixture is poured into water and extracted with EtOAc. The organic layer is separated, dried with MgSO4, then concentrated in vacuo. The residue is purified by flash chromatography [silica gel, hexane:EtOAc/5:5] to provide tert-butyl 4-methyl-3-(3-methyl-1-(6-(methylamino)-pyrimidin-4-yl)-1H-pyrazol-5-ylamino)phenylcarbamate 38.

後処理

  1. customThe mixture is flushed with N2 at 0° C. for a few minutes
  2. additionThe mixture is poured into water
  3. extractionextracted with EtOAc
  4. customThe organic layer is separated
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography [silica gel, hexane:EtOAc/5:5]

出典と根拠

ORDレコード
ord-57452b269d174418bf3a0636d3ad5d55
出典データセット
uspto-grants-2012_06
特許番号
US08202876B2

反応ノート

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