Hydrochloric Acid → HCID 72703519, compound

HRID 1049888Notes

Reaction equation

HRID 1049888 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:18])[C:16]=3[N:17]=2)[CH:5]=[CH:4][N:3]=1.Cl.[OH-:20].[Na+]>O1CCOCC1>[NH2:18][C:15]1[C:16]2[N:17]=[C:8]([C:6]3[CH:5]=[CH:4][NH:3][C:2](=[O:20])[CH:7]=3)[CH:9]=[CH:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 72703518HCID 72703518, compound

Product 1

HCID 72703519HCID 72703519, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

6-(2-fluoro-4-pyridyl)pyrido[3,2-d]pyrimidin-4-amine (50 mg, 0.21 mmol) 1 was treated with hydrogen chloride (4 mol/L) in 1,4-dioxane. The mixture was heated to 80° C. for 1 hour. Cooled to room temperature and basified with 4 N NaOH. Yellow precipitate was collected, and purified with Prep HPLC, 30 mg of 4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)pyridin-2(1H)-one 2 was obtained (yield 60%). LC/MS (ESI+): m/z 240 (M+H). 1H NMR (400 MHz, DMSO) δ 8.39 (d, J=8.7 Hz, 1H), 8.18 (s, 1H), 8.15 (d, J=8.6 Hz, 1H), 7.52 (d, J=6.9 Hz, 1H), 7.11 (d, J=1.6 Hz, 1H), 7.00 (dd, J=6.9, 1.8 Hz, 1H).

Workup

  1. customYellow precipitate was collected
  2. custompurified with Prep HPLC

Sources & evidence

ORD record
ord-5491925756e04005927f4a5d869d2396
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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