Hydrochloric Acid → HCID 67063155, compound

HRID 599275Notes

Reaction equation

HRID 599275 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16]([S:21][CH3:22])=[N:17][CH:18]=3)[N:13]([CH3:23])[C:12]2=[O:24])=[C:4]([CH3:25])[CH:3]=1.Cl>CCO.[Fe]>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([CH3:25])=[C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16]([S:21][CH3:22])=[N:17][CH:18]=3)[N:13]([CH3:23])[C:12]2=[O:24])[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67062983HCID 67062983, compound

Product 1

HCID 67063155HCID 67063155, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

3-(4-fluoro-2-methyl-5-nitrophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (3 g, 8.26 mmol) was added to a solution of HCl (1.6 g, 16.5 mmol) in EtOH (50 ml) followed by iron power (4.6 g, 80 mmol), and the resulting mixture was stirred at 50° C. for 6 hours. The mixture was filtered and the filtrate was neutralized with saturated Na2CO3 solution to pH 8 and the mixture was extracted with EtOAc (3×150 mL). The combined extracts were washed with brine, dried Na2SO4) and evaporated to give 3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.9 g, 67% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.19 (s, 1 H), 6.89 (d, J=12.4 Hz, 1H), 6.65 (d, J=8.8 Hz, 1 H), 5.01 (s, 2 H), 4.62 (d, J=14.8 Hz, 1 H), 4.44 (d, J=14.8 Hz, 1 H), 3.24 (s, 3 H), 2.48 (s, 3 H), 1.92 (s, 3 H); MS (ESI) m/z: 334.1 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe mixture was extracted with EtOAc (3×150 mL)
  3. washThe combined extracts were washed with brine, dried Na2SO4) and
  4. customevaporated

Sources & evidence

ORD record
ord-3d5ca167ea064f6d87b882245da2b35c
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…