Hydrogen Peroxide → 2-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide

HRID 2280754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280754
[C:1]12([NH:6][C:7]3[N:12]=[C:11]([NH:13][C@@H:14]4[CH2:19][CH2:18][C@@H:17]([CH3:20])[C@H:16]([OH:21])[CH2:15]4)[C:10]([C:22]#[N:23])=[CH:9][N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.[OH-:24].[Na+].OO>CS(C)=O>[C:1]12([NH:6][C:7]3[N:12]=[C:11]([NH:13][C@@H:14]4[CH2:19][CH2:18][C@@H:17]([CH3:20])[C@H:16]([OH:21])[CH2:15]4)[C:10]([C:22]([NH2:23])=[O:24])=[CH:9][N:8]=3)[CH2:2][CH:3]([CH2:4]1)[CH2:5]2

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 712373672-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)pyrimidine-5-carbonitrile

Produkt 1

HCID 712370942-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2-(Bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)pyrimidine-5-carbonitrile (0.38 g, 1.213 mmol) was dissolved in DMSO (26.9 mL) and to this solution was added a 50% aqueous sodium hydroxide solution (0.097 ml, 1.213 mmol) and a 30% aqueous hydrogen peroxide solution 0.137 mL, 1.213 mmol) at room temperature. Then the reaction mixture was stirred at 50° C. for 1 h. The reaction was cooled to room temperature and it was poured into 50 mL of ice water. The white precipitate was collected on filter paper and was washed twice with water. The precipitate was dried to give 2-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide (0.269 g, 0.812 mmol, 67% yield). 1H NMR (DMSO-d6, 400 MHz): δ ppm 0.94 (d, J=6.25 Hz, 3H) 1.10-1.26 (m, 3H) 1.68 (d, J=10.54 Hz, 1H) 1.92 (d, J=10.93 Hz, 1H) 2.06 (s, 6H) 2.17 (d, J=9.76 Hz, 1H) 2.46 (s, 1H) 2.98 (br. s., 1H) 3.82-3.95 (m, 1H) 4.63 (br. s., 1H) 7.16 (br. s., 1H) 7.77 (br. s., 1H) 8.11 (br. s., 1H) 8.33 (s, 1H) 9.24 (br. s., 1H); MS (ESI): m/z 332.3 [M+1]+.

Aufarbeitung

  1. customat room temperature
  2. temperatureThe reaction was cooled to room temperature
  3. customThe white precipitate was collected
  4. filtrationon filter paper
  5. washwas washed twice with water
  6. customThe precipitate was dried

Quellen und Nachweise

ORD-Eintrag
ord-fe76691505f24bf8a79758528f14e9dd
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139534B2

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