Ammonium hydroxide isopropanol → 5-Bromo-N4-cyclopentylpyrimidine-2,4-diamine

HRID 79104

反応式

HRID 79104 の反応式
[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH4+:15].[OH-].C(O)(C)C>>[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:15])=[N:6][CH:7]=1

参加物

3

反応物 2

HCID 22611478Ammonium hydroxide isopropanolHCID 442482475-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine

生成物 1

HCID 582998155-Bromo-N4-cyclopentylpyrimidine-2,4-diamine収率 66%

実験手順

A solution of 1 (45 g, 200 mmol) in 28% NH4OH/iso-propanol (1/1, 400 mL) was heated at 120° C. in a sealed tube for 22 h. The product was extracted with dichloromethane and the organic layers were washed with brine and dried. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in hexanes to give the titled compound (2) as a white solid (34 g, 66%). 1H NMR (500 MHz, DMSO-d6) δ 7.77 (1H, s), 6.19 (2H, br. s), 6.12 (1H, d, 1H, J=7.3 Hz), 4.33 (1H, m) 1.90 (2H, m), 1.69 (2H, m), 1.49-1.55 (4H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 257.0, Calculated 257.0.

後処理

  1. extractionThe product was extracted with dichloromethane
  2. washthe organic layers were washed with brine
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-25e649a3c96d4e73859938eb1edb6a41
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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