Sodium Bicarbonate → HCID 178483045, Verbindung

HRID 1526470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526470
Cl.[N:2]1([C:8]2[N:13]=[C:12]([OH:14])[CH:11]=[C:10]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH3:21][N:22]([CH3:31])[C:23]1[N:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][N:24]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.ClCCl>[CH3:21][N:22]([CH3:31])[C:23]1[N:28]=[CH:27][C:26]([CH2:29][N:18]2[CH2:19][CH2:20][CH:15]([C:10]3[N:9]=[C:8]([N:2]4[CH2:7][CH2:6][O:5][CH2:4][CH2:3]4)[N:13]=[C:12]([OH:14])[CH:11]=3)[CH2:16][CH2:17]2)=[CH:25][N:24]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 7955442-(Dimethylamino)-5-pyrimidinecarbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 1784796222-morpholin-4-yl-6-piperidin-4-yl-1H-pyrimidin-4-one;hydrochloride

Produkt 1

HCID 178483045HCID 178483045, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Morpholin-4-yl-6-piperidin-4-yl-pyrimidin-4-ol, hydrochloride salt (0.16 g, 0.47 mmol), 2-dimethylamino-pyrimidine-5-carboxaldehyde (86 mg, 0.57 mmol), and one drop of acetic acid were mixed in dry dichloromethane (10 mL) for 3 hours at room temperature. Sodium cyanoborohydride (88 mg, 1.42 mmol) was added and the mixture stirred for 3 days. The mixture was poured into saturated sodium bicarbonate solution and extracted with dichloromethane (3×50 mL). The material was purified on silica gel, eluting with 10% methanol in dichloromethane to provide 6-[1-(2-Dimethylaminopyrimidin-5-ylmethyl)-piperidin-4-yl]-2-morpholin-4-yl-pyrimidin-4-ol (Compound IIa, 0.11 g, 69% yield) as a white solid. CHN Analysis: Calculated for C20H29N7O2: 60.13; C, 7.32; H, 24.54; N. found 57.31; C, 7.11; H, 23.68; H. Bestfit is C20H29N7O2+1H2O; 57.54; C, 7.48; H, 23.48; N. 1H NMR (300 MHz, CDCl3/CD3OD/TMS): δ=8.26 (s, 2H), 5.65 (s, 1H), 3.85-3.60 (m, 8H), 3.42 (m, 2H), 3.19 (s, 6H), 3.15-2.85 (m, 3H), 2.40-2.00 (m, 2H), 2.18-1.60 (m, 4H). 13C NMR (75 MHz, CDCl3/CD3OD/TMS): δ=173.66, 161.63, 158.91, 153.90, 116.63, 98.76, 66.56, 57.62, 53.12, 44.94, 43.65, 37.48, 30.26.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×50 mL)
  2. customThe material was purified on silica gel
  3. washeluting with 10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-28093f955e1d49079e436c6ee63b45ba
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085585B2

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