HCID 45257321, compound → HCID 178433350, compound

HRID 1917488Notes

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.[NH2:22][O:23][CH2:24][C@@H:25]1[CH2:29][C@@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:27][N:26]1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>[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:22]\[O:23][CH2:24][C@@H:25]2[CH2:29][C@@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:27][N:26]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[N:7]=1

Participants

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 (183 mg, 0.5 mmol), (2S,4R)-tert-butyl 2-(aminooxymethyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate (692 mg, 2.0 mmol), Hg(OAc)2 (320 mg, 1.0 mmol) and toluene (2 mL) was heated at 100° C. for 2 h. Cooled to r.t., filtered through celite and purified to afford (2S,4R)-tert-butyl 2-(((Z)—((R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5-(6H)-ylidene)aminooxy)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate (200 mg, 50%) as off white solid. MS (ES) [M+H] calculated for C30H45BrFN6O4Si, 679.24; found 679.20.

Workup

temperatureCooled to r.t.
filtrationfiltered through celite
custompurified

Sources & evidence

ORD record: ord-7aa0361da43c4141967c2c1accb27a4f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618290B2

Reaction notes

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