Lithium hydroxide, monohydrate → HCID 21069858, compound

HRID 348116Notes

Reaction equation

HRID 348116 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([O:24]CC)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>C(O)C.O1CCCC1>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([OH:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21069952Ethyl 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate

Product 1

HCID 21069858HCID 21069858, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of intermediate 26, ethyl 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate, (2.93 g, 8.2 mmol) and LiOH.H2O (0.84 g, 20 mmol) in 4:1 ethanol/tetrahydrofuran (50 mL) was stirred for 2 h at ambient temperature then concentrated under vacuum. The resulting yellow residue was treated with 1N HCl (25 mL) providing a precipitate that was filtered and dried under vacuum to yield the title compound as a white powder (2.68 g, 99% yield). 1H NMR (500 MHz, CDCl3) δ ppm: 7.54–7.48 (2H, m), 7.37–7.27 (3H, m), 5.44 (2H, s), 4.05–3.93 (4H, m), 1.60 (6H, s).). HRMS (M+H) calcd for C17H19N2O5: 331.1294; found: 331.1308. Anal calcd for C17H18N2O5: C, 61.81; H, 5.49; N, 8.48; found: C, 61.84; H, 5.36; N, 8.25.

Workup

  1. concentrationthen concentrated under vacuum
  2. additionThe resulting yellow residue was treated with 1N HCl (25 mL)
  3. customproviding a precipitate that
  4. filtrationwas filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f3963eb827d7478d8d70ca53184860f4
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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