Hydrochloric Acid → HCID 178466037, compound

HRID 924875Notes

Reaction equation

HRID 924875 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:17][C:16](=S)[NH:15]2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:44][NH2:45].[O-]S([O-])=O.[Na+].[Na+].Cl>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:17]/[C:16](=[N:45]\[CH3:44])/[NH:15]2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 51347328HCID 51347328, compound2×

Product 1

HCID 178466037HCID 178466037, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of crude 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyrimidine-2(1H)-thione (Compound 8) (392 mg, 0.877 mmol), m-CPBA (887 mg of 85% purity, 4.38 mmol) and aqueous methylamine solution (3 mL) in ethanol (20 mL) was stirred at 0° C. for 2 h, then at room temperature overnight. Na2SO3 (2 g) was added and then dilute hydrochloride acid was added drop wise to adjust the pH to about 6. The above mixture was extracted with ethyl acetate (40 mL×3), dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography, followed by preparative HPLC twice to afford Compound 117 (26 mg, yield: 6.7%). 1H NMR (DMSO-d6 400 MHz): δ 8.73 (s, 1H), 7.83 (d, J=7.2 Hz, 1H), 7.53 (s, 1H), 7.48 (s, 2H), 7.33 (s, 4H), 7.10-7.11 (m, 3H), 7.01 (s, 1H), 6.89-6.91 (m, 3H), 5.22 (s, 1H), 3.93 (d, J=6.8 Hz, 1H), 2.78 (s, 3H), 1.24-1.27 (t, J=4.8 Hz, 3H); MS (ESI): m/z 445.2[M+1]+.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionThe above mixture was extracted with ethyl acetate (40 mL×3)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b664381005ae48f2b754d6e01ddaedd6
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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