Ammonia → HCID 66956832, compound

HRID 2066646Notes

Reaction equation

HRID 2066646 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH2:9][CH:8]([CH2:13][O:14][Si](C(C)C)(C(C)C)C(C)C)[O:7]2)([O-:3])=[O:2].Cl.C(=O)=O.CC(C)=O.N>CCO.CO>[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH2:9][CH:8]([CH2:13][OH:14])[O:7]2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 18522661Acetone cardiceHCID 66956631HCID 66956631, compound

Product 1

HCID 66956832HCID 66956832, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A suspension of silyl ether 133 (1.627 g, 4.58 mmol) in a solution of 1% HCl in 95% EtOH (desilylation conditions described by Cunico et al., 1980) (58 mL) was stirred at room temperature for 35 h. The resulting solution was cooled (CO2/acetone), neutralised by dropwise addition of 7 M NH3 in MeOH (7 mL) with stirring, and then concentrated to dryness and the residue was chromatographed on silica gel. Elution with 0-2% MeOH/CH2Cl2 firstly gave foreruns, and then further elution with 2% MeOH/CH2Cl2 gave (2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-yl)methanol (134) (877 mg, 96%) as a pale yellow solid: mp (THF/MeOH/CH2Cl2/hexane) 179-181° C.; 1H NMR [(CD3)2SO] δ 8.04 (s, 1H), 5.12 (t, J=5.8 Hz, 1H), 4.48 (dtd, J=10.2, 4.7, 2.5 Hz, 1H), 4.13 (ddd, J=12.5, 5.8, 3.0 Hz, 1H), 4.04 (ddd, J=12.4, 11.0, 5.1 Hz, 1H), 3.64 (m, 2H), 2.18 (dtd, J=14.4, 5.0, 2.8 Hz, 1H), 2.03 (dtd, J=14.4, 10.6, 5.7 Hz, 1H). Anal. (C7H9N3O4) C, H, N.

Workup

  1. stirringwith stirring
  2. concentrationconcentrated to dryness
  3. customthe residue was chromatographed on silica gel
  4. washElution with 0-2% MeOH/CH2Cl2 firstly gave foreruns
  5. washfurther elution with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c1b9eb53c32142fb81e7dc2c8864c70b
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

Loading…