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2-Aminopyrimidine-5-carbaldehyde → 5-(((trans)-2-(4-(Benzyloxy)phenyl)cyclopropylamino)methyl)pyrimidin-2-amine

HRID 709415
ノート
印刷プレビュー

反応式

HRID 709415 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]2[CH2:31][C@H:30]2[NH2:32])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:33][C:34]1[N:39]=[CH:38][C:37]([CH:40]=O)=[CH:36][N:35]=1.[BH4-].[Na+]>ClCCCl>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([C@@H:29]2[CH2:31][C@H:30]2[NH:32][CH2:40][C:37]2[CH:36]=[N:35][C:34]([NH2:33])=[N:39][CH:38]=2)=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
参加物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 7690972-Aminopyrimidine-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 51888238(1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine2 回

生成物 1

HCID 566399155-(((trans)-2-(4-(Benzyloxy)phenyl)cyclopropylamino)methyl)pyrimidin-2-amine収率 25%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Sodium triacetoxy borohydride (883 mg, 4.166 mmol) was added slowly at 0° C. to a solution of (trans)-2-(4-(benzyloxy)phenyl)cyclopropanamine (Intermediate B, 500 mg, 2.083 mmol), 2-aminopyrimidine-5-carbaldehyde (256 mg, 2.083 mmol) in DCE (10 mL) and stirred for 20 h. After completion, the solvent was evaporated. The residue was dissolved in Methanol (15 mL), NaBH4 (237 mg, 6.249 mmol) was added slowly at 0° C. and stirred for 3 h. After completion, the solvent was evaporated, the residue was dissolved in ice water (20 mL) and extracted with EtOAc (2×20 mL) The combined organic layers were washed with brine (20 mL) and dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by prep HPLC to afford 5-(((trans)-2-(4-(benzyloxy)phenyl)cyclopropylamino)methyl)pyrimidin-2-amine (180 mg, 25%) as white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.85 (q, 1H), 0.90 (quin, 1H), 1.73 (m, 1H), 2.07 (m, 1H), 2.75 (brs, 1H), 3.53 (s, 2H), 5.04 (s, 2H), 6.46 (s, 2H), 6.85 (d, 2H), 6.92 (d, 2H), 7.33 (m, 1H), 7.42 (m, 4H), 8.11 (s, 2H). Mass (M+H): 347.3

後処理

  1. customAfter completion, the solvent was evaporated
  2. dissolutionThe residue was dissolved in Methanol (15 mL)
  3. stirringstirred for 3 h
  4. customAfter completion, the solvent was evaporated
  5. dissolutionthe residue was dissolved in ice water (20 mL)
  6. extractionextracted with EtOAc (2×20 mL) The combined organic layers
  7. washwere washed with brine (20 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude residue was purified by prep HPLC

出典と根拠

ORDレコード
ord-90deeaf7b94a43318bda5dad4b3998a2
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181198B2

反応ノート

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