Ammonia → 2-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1930313Notes

Reaction equation

HRID 1930313 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:18]([CH:21]([CH3:23])[CH3:22])[C:11]3[N:12]=[C:13](SC)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].C1C=C(Cl)C=C(C(OO)=O)C=1.[NH3:38]>O1CCOCC1>[NH2:38][C:13]1[N:14]=[CH:15][C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N+:24]([O-:26])=[O:25])[CH:4]=3)[C:19](=[O:20])[N:18]([CH:21]([CH3:23])[CH3:22])[C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 70297m-Chloroperbenzoic acidHCID 689848066-(4-fluoro-3-nitrophenyl)-8-isopropyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 692975172-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-oneYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using a procedure analogous to Example A1, 6-(4-fluoro-3-nitrophenyl)-8-isopropyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.82 g, 2.2 mmol), MCPBA (0.38 g, 2.2 mmol) and 0.5 M ammonia in dioxane (8 mL) were combined to afford 2-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one as a yellow solid (0.52 g, 69% yield). 1H NMR (400 MHz, MeOH-d4): δ 8.61 (s, 1H), 8.44 (dd, J=7.6 Hz, 2.4 Hz, 1H), 8.03-8.00 (m, 1H), 7.95 (s, 1H), 7.48 (dd, J=10.8 Hz, 7.6 Hz, 1H), 5.96-5.92 (m, 1H), 2.63 (s, 3H), 1.64 (d, J= 6.4 Hz, 6H); MS (ESI) m/z: 344.3 (M+H+).

Sources & evidence

ORD record
ord-fbb5d26dfcf54e00a83da5a97d3b41a0
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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