3-Methyluracil → 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

HRID 1182661

Reaktionsgleichung

Reaktionsgleichung von HRID 1182661
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][NH:4][C:3]1=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[OH:38][C@@H:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[NH2:44].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[OH:38][C@@H:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[NH:44][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[CH:5][N:4]=1

Komponenten

6

Edukt 4

HCID 790663-MethyluracilHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12886906(1R,2R)-2-aminocyclopentan-1-ol hydrochloride

Produkt 1

HCID 673709162-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-oneAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Methyluracil (12.6 mg, 0.1 mmol) was dissolved in 0.5 mL of DMF, and then BOP (71 mg, 0.16 mmol) was added. The mixture was stirred at room temperature for two minutes, then (1R,2R)-(−)-2-hydroxycyclopentylamine hydrochloride salt (22 mg, 0.16 mmol) was added, followed by DBU (51 uL, 3.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was purified by a semi-preparative HPLC to give pure product (16 mg, yield 76%). MS (ESI) m/z 210.1 [M+H]+.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was purified by a semi-preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b91a2c85966e4a2ba3dd38e25348a084
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664207B2

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