Bromomethylcyclopropane → 2-Chloro-5-(cyclopropylmethyl)-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169554
[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[NH:8][CH2:7][CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.[CH3:17][C:18]([CH3:21])([O-])[CH3:19].[Na+].BrCC1CC1>CS(C)=O>[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[N:8]([CH2:17][CH:18]3[CH2:21][CH2:19]3)[CH2:7][CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 81503BromomethylcyclopropaneHCID 23676156Sodium t-butoxideHCID 866701002-Chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Produkt 1

HCID 866701022-Chloro-5-(cyclopropylmethyl)-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridineAusbeute 18,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a round-bottom flask was added 2-chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x20, 248 mg, 1.030 mmol) in DMSO (4 mL). Sodium tert-butoxide (119 mg, 1.236 mmol) was added, followed by (bromomethyl)cyclopropane (0.105 mL, 1.082 mmol), and the reaction mixture was stirred overnight at room temperature. The mixture was subsequently filtered and the filtrate was purified by preparatory HPLC using a gradient of 25-50% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). The fractions were collected and concentrated in vacuo to give the title compound as a brown solid (56 mg, 0.190 mmol, 18%). ESI-MS m/z [M+H]+ calc'd for C14H19ClN4O, 295.12; found 295.6.

Aufarbeitung

  1. filtrationThe mixture was subsequently filtered
  2. customthe filtrate was purified by preparatory HPLC
  3. customThe fractions were collected
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eb7885bd26d24383b9f7dbed7678c405
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045496B2

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