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Triethylamine → (S)-4-(2-chloro-6-(cyclopropylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

HRID 1626558
ノート
印刷プレビュー

反応式

HRID 1626558 の反応式
Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][NH:10][CH2:9][C:7]=2[N:8]=1.[CH:19]1([CH:22]=O)[CH2:21][CH2:20]1.CCN(CC)CC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][N:10]([CH2:22][CH:19]3[CH2:21][CH2:20]3)[CH2:9][C:7]=2[N:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86663150(S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride2 回

生成物 1

HCID 86663153(S)-4-(2-chloro-6-(cyclopropylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine収率 94.9%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
20 °C

実験手順

To a stirring solution of (S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride (intermediate 6) (870 mg, 3.01 mmol) in dichloroethane, was added cyclopropanecarboxaldehyde (450 uL, 6.02 mmol) and Et3N (840 uL, 6.02 mmol). The reaction mixture was stirred at room temperature (20° C.) for 45 minutes, before adding sodium triacetoxy borohydride (1.28 g, 6.02 mmol). The reaction mixture was then stirred for a further 2 h at room temperature (20° C.) before partitioning between saturated NaHCO3 solution and DCM. The organic layer was recovered, dried over MgSO4, filtered and the solvent removed in vacuo, affording the title compound as a colourless oil (882 mg, 92% yield).

後処理

  1. stirringThe reaction mixture was then stirred for a further 2 h at room temperature (20° C.)
  2. custombefore partitioning between saturated NaHCO3 solution and DCM
  3. customThe organic layer was recovered
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-d76bff86ecf84485b2a420daac7030bd
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785457B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート