Acetaldehyde → 1-[6-ethylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1428880ノート

反応式

HRID 1428880 の反応式
[CH:1](=O)[CH3:2].[CH2:4]([O:6][C:7]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22](=[O:32])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH2:33])[CH:20]=3)[N:15]=2)[CH:13]=1)=[O:8])[CH3:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C.CCOC(C)=O>[CH2:4]([O:6][C:7]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22](=[O:32])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:33][CH2:1][CH3:2])[CH:20]=3)[N:15]=2)[CH:13]=1)=[O:8])[CH3:5]

参加物

6

反応物 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 684879131-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

生成物 1

HCID 684855101-[6-ethylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester収率 33%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Acetaldehyde (1 mL) was added to 1-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.250 g, 0.582 mol) and 4 Å molecular sieves (0.35 g) in ethanol (1.9 g). The reaction mixture was stirred at room temperature for 18 h and was then filtered. Ethanol and acetaldehyde were removed under high vacuum. The residue was redissolved in DCE (1.5 mL) and sodium triacetoxyborohydride (0.308 g, 1.46 mmol) was added. The reaction mixture was stirred at room temperature for 6 d, then diluted with EtOAc (30 mL) and washed with saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was extracted with EtOAc (30 mL) and the combined organic layers were washed with brine (20 mL), dried (MgSO4), and concentrated. The residue was purified via FCC (5-65% EtOAc/hexanes) to yield the titled compound (87.0 mg, 33% yield). MS (ESI/Cl): mass calcd. for C22H31N5O4Si, 457.2; m/z found, 458.2 [M+H]+.

後処理

  1. filtrationwas then filtered
  2. customEthanol and acetaldehyde were removed under high vacuum
  3. dissolutionThe residue was redissolved in DCE (1.5 mL)
  4. stirringThe reaction mixture was stirred at room temperature for 6 d
  5. washwashed with saturated aqueous sodium bicarbonate (20 mL)
  6. extractionThe aqueous layer was extracted with EtOAc (30 mL)
  7. washthe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified via FCC (5-65% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-13a8f5857df54754b9b2807d5a1a8379
出典データセット
uspto-grants-2015_01
特許番号
US08937078B2

反応ノート

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