Ammonia → HCID 58577901, compound

HRID 473970Notes

Reaction equation

HRID 473970 reaction equation
Cl[C:2]1[C:7]2[C:8](=[O:28])[N:9]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[N:17][CH:18]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1.[NH3:29]>O1CCOCC1>[NH2:29][C:2]1[C:7]2[C:8](=[O:28])[N:9]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[N:17][CH:18]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58577897HCID 58577897, compound

Product 1

HCID 58577901HCID 58577901, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-(5-(4-chloro-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)pyridin-2-yloxy)-2,2-dimethylpropanoate B-20 was dissolved in a 0.5 M solution of ammonia in 1,4-dioxane and stirred at room temperature for 20 h. The reaction mixture was then concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica gel (7 N ammonia solution in methanol:CH2Cl2 gradient) to give methyl 3-(5-(4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)pyridin-2-yloxy)-2,2-dimethylpropanoate B-21 (55.0 mg, Yield=57% from B-19). MS (ESI) [M+1]+ 388.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
  2. customThe residue was purified by flash column chromatography on silica gel (7 N ammonia solution in methanol:CH2Cl2 gradient)

Sources & evidence

ORD record
ord-b848624e855c46a7ba1ad9a7829e34c6
Source dataset
uspto-grants-2014_01
Patent number
US08637507B2

Reaction notes

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