Trimethyl orthoformate → HCID 86710193、化合物

HRID 2284431ノート

反応式

HRID 2284431 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][C:6]=2[N:7]=1.[OH:20][CH:21]([CH3:30])[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23].C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH2:12][N:27]3[CH2:26][CH2:25][N:24]([C:22](=[O:23])[CH:21]([OH:20])[CH3:30])[CH2:29][CH2:28]3)=[CH:8][C:6]=2[N:7]=1

参加物

7

反応物 4

HCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 13460159Piperazine, 1-(2-hydroxy-1-oxopropyl)- (9CI)HCID 86710192HCID 86710192、化合物

生成物 1

HCID 86710193HCID 86710193、化合物収率 35.6%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

In a 50 mL round bottom flask, 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-7-carbaldehyde (0.3 g, 0.0010 mol) and 1,2-dichloroethane (20 mL) were added. To the reaction flask, 2-hydroxy-1-(piperazin-1-yl)propan-1-one (0.204 g, 0.0013 mol) and trimethyl orthoformate (0.228 g, 0.0030 mol) were added and the reaction mixture stirred at room temperature for 12 hours. To the reaction mixture, sodium triacetoxyborohydride (g, 0.683 0.0020 mol) was added and stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform) to provide the title compound (0.15 g, 33%). 1H NMR (300 MHz, CDCl3): δ 8.62 (d, J=1.8 Hz, 1H), 7.86 (d, J=1.2 Hz, 1H), 4.72 (br s, 4H), 3.84 (t, J=9.0 Hz, 4H), 3.65 (s, 2H), 3.60-3.52 (m, 1H), 3.41 (d, J=2.7 Hz, 1H), 3.23 (s, 4H), 2.46 (d, J=3.0 Hz, 4H), 1.27 (d, J=6.6 Hz, 3H): LC-MS (ESI): Calculated mass. 420.1, Observed mass [M+H]+: 421.1 (RT=0.24 min).

後処理

  1. stirringstirred at room temperature for 3 hours
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto provide the crude product
  6. customThe crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform)

出典と根拠

ORDレコード
ord-4bda41f29c4441d5ba2dd55927fcb93f
出典データセット
uspto-grants-2015_09
特許番号
US09145411B2

反応ノート

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