Trifluoroacetic acid water → HCID 178433358, compound

HRID 656607Notes

Reaction equation

HRID 656607 reaction equation
[Si]([O:8]/[N:9]=[C:10]1\[NH:11][C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[Br:29])[CH2:13][C:14]2[N:15]=[C:16]([NH2:21])[N:17]=[C:18]([CH3:20])[C:19]\1=2)(C(C)(C)C)(C)C.C(O)(C(F)(F)F)=O.O>O1CCOCC1>[NH2:21][C:16]1[N:17]=[C:18]([CH3:20])[C:19]2=[C:14]([CH2:13][C@H:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[Br:29])[NH:11]/[C:10]/2=[N:9]\[OH:8])[N:15]=1

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 178433359HCID 178433359, compound

Product 1

HCID 178433358HCID 178433358, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R,Z)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one O-tert-butyldimethylsilyloxime (85b, 384 mg, 0.8 mmol) in dioxane (2 mL) was added 1:9 TFA-H2O and the reaction mixture stirred at room temperature for 2 h. The resulting solid was filtered and washed with dioxane, then dried to afford (R,Z)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one oxime (85c, 206 mg, 70%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.56 (s, 3H) 2.83 (dd, J=15.92, 4.55 Hz, 1H) 3.17 (dd, J=16.04, 5.94 Hz, 1H) 4.90 (q, J=4.97 Hz, 1H) 7.20 (d, J=1.52 Hz, 1H) 7.21-7.23 (m, 1H) 7.57 (ddd, J=8.34, 1.64, 1.39 Hz, 1H) 9.82 (s, 1H). MS (ES) [M+H] calculated for C14H14BrFN5O, 366.03. found 366.20.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with dioxane
  3. customdried

Sources & evidence

ORD record
ord-4b8e70d726404b6b9398464dbbbf1200
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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