HCID 45257321, compound → HCID 178501472, compound

HRID 656587Notes

Reaction equation

HRID 656587 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[C:11](=S)[NH:10][C@@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[Br:20])[CH2:8][C:6]=2[N:7]=1.O=C1C2C(=CC=CC=2)C(=O)[N:24]1[O:33][CH2:34][CH2:35][C@H:36]([O:41][CH3:42])[C:37]([O:39][CH3:40])=[O:38]>[Hg](OC(C)=O)OC(C)=O.C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2=[C:6]([CH2:8][C@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[Br:20])[NH:10]/[C:11]/2=[N:24]\[O:33][CH2:34][CH2:35][C@H:36]([O:41][CH3:42])[C:37]([O:39][CH3:40])=[O:38])[N:7]=1

Participants

5

Reactant 2

HCID 45257321HCID 45257321, compoundHCID 67065361(S)-methyl 4-(1,3-dioxoisoindolin-2-yloxy)-2-methoxybutanoate

Product 1

HCID 178501472HCID 178501472, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-5(6H)-thione (31I, 146 mg, 0.4 mmol), (S)-methyl 4-(aminooxy)-2-methoxybutanoate (46c, 260 mg, 1.6 mmol), Hg(OAc)2 (257 mg, 0.8 mmol) and toluene (2 mL) was heated at 100° C. for 2 h. Cooled to rt, filtered through celite and purified to afford (S)-methyl 4-((Z)—((R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylidene)aminooxy)-2-methoxybutanoate (23 mg, 12%) as off white solid. MS (ES) [M+H] calculated for C20H24BrFN5O4, 496.09. found 496.20.

Workup

  1. temperatureCooled to rt
  2. filtrationfiltered through celite
  3. custompurified

Sources & evidence

ORD record
ord-c3571b83269448919451924241df2bc3
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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