Sodium Carbonate → HCID 178513290, compound

HRID 924860Notes

Reaction equation

HRID 924860 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:3]1.[NH2:28][OH:29].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[OH:29][NH:28][C:11](=[NH:12])[C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([CH:6]2[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:4]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:3][C:2](=[O:1])[NH:7]2)[CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 67060962HCID 67060962, compound

Product 1

HCID 178513290HCID 178513290, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(2-oxo-5,6-diphenyl-1,2,3,4-tetrahydropyrimidin-4-yl)benzonitrile (700 mg, 2 mmol, 1 eq), NH2OH—HCl (144 mg, 2.2 mmol, 1.1 eq) and Na2CO3 (414 mg, 4.0 mmol, 2.0 eq) in methanol (5.0 mL) was heated to reflux overnight. The mixture was cooled to room temperature and filtered. The filtered mass was washed with methanol (5.0 mL) and purified by prep-HPLC to afford Compound 99 as a yellow solid (150 mg, 19.5%) and Compound 98 as a white solid (6.7%). Data for Compound 99: 1H NMR (MeOH-d4 500 MHz TMS): δ 7.69-7.72 (m, 2H), 7.58-7.61 (m, 2H), 7.26 (br, 5H), 7.04 (br, 2H), 6.88 (br, 2H), 5.51 (s 1H); MS (ESI): m/z 385.1.1 [M+1]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. washThe filtered mass was washed with methanol (5.0 mL)
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-bf4ff568c6954c4893f711678db13da6
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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