Sodium Carbonate → 5-(2-Aminopyrimidin-5-yl)picolinic acid

HRID 500178ノート

反応式

HRID 500178 の反応式
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=2)O1.C[O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](Br)=[CH:29][N:28]=1)=[O:26]>O.C(O)C.C1(C)C=CC=CC=1.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>[NH2:21][C:18]1[N:19]=[CH:20][C:15]([C:30]2[CH:31]=[CH:32][C:27]([C:25]([OH:26])=[O:24])=[N:28][CH:29]=2)=[CH:16][N:17]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 7016458Methyl 5-bromopyridine-2-carboxylateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol ester

生成物 1

HCID 672237795-(2-Aminopyrimidin-5-yl)picolinic acid収率 58%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

Sodium carbonate (0.636 g, 6.0 mmol) in water (2.0 mL) was added to a mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.442 g, 2.0 mmol), 5-bromopyridine-2-carboxylic acid methyl ester (0.518 g, 2.4 mmol) and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) in ethanol (3.0 mL) and toluene (3.0 mL). The resulting mixture was heated at 120° C. for 3 h. The organic solvents were removed under reduced pressure. The residue was diluted with water, and adjusted with 1N HCl to pH=4. The precipitates were collected by filtration, washed with water and EtOAc, and dried to give the desired product (0.25 g, 58%). LCMS: (M+H)=217.0.

後処理

  1. customThe organic solvents were removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water and EtOAc
  5. customdried

出典と根拠

ORDレコード
ord-3ed1e76a009e4a60ad1ea18cc7432f40
出典データセット
uspto-grants-2010_08
特許番号
US07767675B2

反応ノート

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