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5-(Chloromethyl)-3-ethyl-1,2-oxazole → (R)-2-chloro-5-((3-ethylisoxazol-5-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 1631746
Notes
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Reaction equation

HRID 1631746 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][C@@H: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:28][N:27]=[C:26]([CH2:29][CH3:30])[CH:25]=1>CS(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:23][C:24]3[O:28][N:27]=[C:26]([CH2:29][CH3:30])[CH:25]=3)[CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 123646005-(Chloromethyl)-3-ethyl-1,2-oxazoleHCID 23676156Sodium t-butoxideHCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 86670130(R)-2-chloro-5-((3-ethylisoxazol-5-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x5 using (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 100 mg, 0.441 mmol) in DMSO (5 mL), sodium tert-butoxide (50.9 mg, 0.529 mmol) and 5-(chloromethyl)-3-ethylisoxazole (70.7 mg, 0.485 mmol) (120 mg, 81%). ESI-MS m/z [M+H]+ calc'd for C15H18ClN5O2, 336.12. found 336.3.

Sources & evidence

ORD record
ord-6669f8d655bf474a81237187f13b046d
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791107B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes