Triethylamine → 4-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acid

HRID 871860

反応式

HRID 871860 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(OCC)(=O)C>C1COCC1>[C:26]([O:25][C:24]([NH:23][CH2:22][CH2:21][CH2:20][NH:19][C:6]1[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)=[O:30])([CH3:29])([CH3:28])[CH3:27]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acid

生成物 1

HCID 866731374-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acid収率 88.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2.21 g (11.45 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid prepared in step 2.3 (method B) in 20 mL of anhydrous THF is cooled to 2-5°C. on an ice bath. A solution of 4.79 mL (34.35 mmol) of triethylamine and 2 g (11.48 mmol) of tert-butyl (3-aminopropyl)carbamate in 15 mL of anhydrous THF is then added dropwise. The reaction mixture is stirred at room temperature for 30 minutes. Ethyl acetate is added and the organic phase is washed with aqueous 1N HCl and with water. The organic phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum. 3.35 g of the expected product are obtained in the form of a yellow solid. Yield=88.6%.

後処理

  1. washthe organic phase is washed with aqueous 1N HCl and with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1a9afc175b754b5ea5efbc5e0b1ac308
出典データセット
uspto-grants-2015_03
特許番号
US08975250B2

関連ノート

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