Sodium t-butoxide → HCID 86670106, compound

HRID 2169558Notes

Reaction equation

HRID 2169558 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.CC(C)([O-])C.[Na+].Cl[CH2:23][C:24]1[O:25][C:26]([CH:29]2[CH2:31][CH2:30]2)=[N:27][N:28]=1>CS(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:23][C:24]3[O:25][C:26]([CH:29]4[CH2:31][CH2:30]4)=[N:27][N:28]=3)[CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 280639572-(Chloromethyl)-5-cyclopropyl-1,3,4-oxadiazoleHCID 86670087HCID 86670087, compound

Product 1

HCID 86670106HCID 86670106, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x9 using 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 75 mg, 0.331 mmol) in DMSO (2 mL) followed by sodium tert-butoxide (35.0 mg, 0.364 mmol) and 2-(chloromethyl)-5-cyclopropyl-1,3,4-oxadiazole (68.2 mg, 0.430 mmol). 1H NMR (400 MHz, DMSO-d6) δ 0.92-1.00 (m, 2 H), 1.07-1.16 (m, 2 H), 2.14-2.25 (m, 1 H), 2.92-3.03 (m, 1 H), 3.03-3.11 (m, 1 H), 3.11-3.20 (m, 1 H), 3.34-3.51 (m, 1 H), 3.53-3.58 (m, 1 H), 3.59-3.72 (m, 1 H), 3.85-4.00 (m, 2 H), 4.20-4.29 (m, 1 H), 4.53-4.63 (m, 1 H), 4.79-4.88 (m, 1 H), 7.56 (s, 1 H). ESI-MS m/z [M+H]+ calc'd for C15H17ClN6O2, 348.11; found 348.2.

Sources & evidence

ORD record
ord-2285723f26ec477fae31c6c6ce6a932c
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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