Ammonia → HCID 66955363, compound

HRID 2066656Notes

Reaction equation

[CH3:1][C:2]1([CH2:14][O:15][Si](C(C)C)(C(C)C)C(C)C)[O:7][C:6]2=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]2[CH2:4][CH2:3]1.Cl.C(=O)=O.CC(C)=O.N.C([O-])(O)=O.[Na+]>CCO.CO>[CH3:1][C:2]1([CH2:14][OH:15])[O:7][C:6]2=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 44 °C

Procedure

A suspension of silyl ether 148 (2.518 g, 6.81 mmol) in a solution of 1% HCl in 95% EtOH (desilylation conditions described by Cunico et al., 1980) (90 mL) was stirred at 44° C. for 3 days. The resulting solution was cooled (CO2/acetone), neutralised by dropwise addition of 7M NH3 in MeOH (8 mL) and NaHCO3 (0.10 g, 1.19 mmol) with stirring, and then concentrated to dryness and the residue was chromatographed on silica gel. Elution with 0-1% MeOH/CH2Cl2 firstly gave foreruns, and then further elution with 1.5% MeOH/CH2Cl2 gave (7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-yl)methanol (149) (1.285 g, 88%) as a pale yellow solid: mp (MeOH/CH2Cl2/hexane) 199-201° C.; 1H NMR [(CD3)2SO] δ 8.03 (s, 1H), 5.22 (t, J=5.7 Hz, 1H), 4.13 (dt, J=12.9, 6.0 Hz, 1H), 4.05 (ddd, J=13.0, 8.1, 5.6 Hz, 1H), 3.54 (dd, J=11.6, 5.5 Hz, 1H), 3.48 (dd, J=11.6, 5.8 Hz, 1H), 2.21 (ddd, J=14.4, 8.1, 5.9 Hz, 1H), 2.00 (dt, J=14.4, 5.8 Hz, 1H), 1.32 (s, 3H). Anal. (C8H11N3O4) C, H, N.

Workup

stirringwith stirring
concentrationconcentrated to dryness
customthe residue was chromatographed on silica gel
washElution with 0-1% MeOH/CH2Cl2 firstly gave foreruns
washfurther elution with 1.5% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-d2256fea85a2441280cf10b768cb732c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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