Hydrochloric Acid → HCID 67063051, compound

HRID 599280Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[N:12]1[CH2:21][C:20]2[C:15](=[N:16][C:17]([S:22][CH3:23])=[N:18][CH:19]=2)[N:14]([CH3:24])[C:13]1=[O:25].Cl>CCO.[Fe]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Cl:1])=[C:3]([N:12]2[CH2:21][C:20]3[C:15](=[N:16][C:17]([S:22][CH3:23])=[N:18][CH:19]=3)[N:14]([CH3:24])[C:13]2=[O:25])[CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(2-chloro-4-fluoro-5-nitrophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.4 g, 3.7 mmol) in EtOH (30 mL) was added conc. HCl (0.75 g, 9 mmol), followed by active iron power (2 g, 36 mmol). The reaction was stirred at 50° C. for 6 hours. The reaction was filtered and the filtrate was diluted with water and treated with saturated aq Na2CO3 solution until pH 8. The aqueous mixture was extracted with EtOAc (3×80 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give 3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.08 g, 84% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.25 (s, 1 H), 7.30 (d, J=11.2 Hz, 1 H), 6.84 (d, J=8.8 Hz, 1 H), 5.50 (s, 2 H), 4.66 (d, J=14.6 Hz, 1 H), 4.53 (d, J=14.6 Hz, 1 H), 3.27 (s, 3 H), 2.51 (s, 3 H); MS (ESI) m/z: 354.3 [M+H]+.

Workup

filtrationThe reaction was filtered
additionthe filtrate was diluted with water
additiontreated with saturated aq Na2CO3 solution until pH 8
extractionThe aqueous mixture was extracted with EtOAc (3×80 mL)
dry with materialThe combined extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1600beb19fd045ffbbff3e06864e7c59
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

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