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

HRID 709415
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 709415
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
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Komponenten

6

Edukt 4

HCID 7690972-Aminopyrimidine-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 51888238(1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-90deeaf7b94a43318bda5dad4b3998a2
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181198B2

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