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Sodium Carbonate → Methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)-2-methoxybenzoate

HRID 1410023
ノート
印刷プレビュー

反応式

HRID 1410023 の反応式
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:22][O:23][C:24]1[CH:33]=[C:32]([NH:34][C:35](=[O:51])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38](B3OC(C)(C)C(C)(C)O3)[CH:37]=2)[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([NH:11][C:4]2[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=[C:2]([C:38]3[CH:37]=[C:36]([CH:41]=[CH:40][CH:39]=3)[C:35]([NH:34][C:32]3[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([O:23][CH3:22])[CH:33]=3)=[O:51])[N:3]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 68379343HCID 68379343、化合物HCID 715341855-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine

生成物 1

HCID 68379396Methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)-2-methoxybenzoate収率 64%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (155 mg, 0.48 mmol) and methyl 2-methoxy-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate (180 mg, 0.44 mmol) in 10 mL of 1,4-dioxane and 1 mL of water was added Na2CO3 (140 mg, 1.32 mmol) followed by Pd(PPh3)4 (26 mg) under nitrogen with stirring. The mixture was refluxed for 15 hours under nitrogen. After cooled, the solvent was evaporated by rotary evaporation. The residue was purified by column chromatography on silica gel eluting with (petroleum ether:EtOAc=1:1) to give methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)-2-methoxybenzoate (160 mg, 64%) as solid. LC-MS: 572 [M+H]+, tR=1.62 min.

後処理

  1. temperatureThe mixture was refluxed for 15 hours under nitrogen
  2. temperatureAfter cooled
  3. customthe solvent was evaporated by rotary evaporation
  4. customThe residue was purified by column chromatography on silica gel eluting with (petroleum ether:EtOAc=1:1)

出典と根拠

ORDレコード
ord-1c81ba56252545c4914916bbb5b824fa
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921383B2

反応ノート

読み込み中…

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