Ethanol → HCID 86692838, compound

HRID 928248Notes

Reaction equation

HRID 928248 reaction equation
[C:1]1([C:11]2[CH:15]=[C:14]([NH2:16])[NH:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:17](OC)(=O)[CH2:18][C:19](OC)=O.C(O)C.C[O-].[Na+].CO>>[C:1]1([C:11]2[CH:15]=[C:14]3[N:16]=[CH:17][CH:18]=[CH:19][N:13]3[N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 887MethanolHCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 178507272HCID 178507272, compound

Product 1

HCID 86692838HCID 86692838, compound

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(1-naphthyl)-1H-pyrazol-5-amine (654 mg, 3.12 mmol) and dimethyl malonate (0.394 mL, 3.44 mmol) in anhydrous ethanol (9.44 mL, 162 mmol) is added 0.5 M sodium methoxide in methanol (12.5 mL, 6.25 mmol). The mixture is heated at 120° C. under a nitrogen atmosphere overnight. The reaction mixture is cooled to room temperature and the solvent is removed in vacuo. The residue is suspended in water and the precipitate is collected in a Buchner funnel to provide 2-(1-naphthyl)pyrazolo[1,5-a]pyrimidine, 7-diol (534 mg, yield 62%). LCMS: (AA) M+1 278; 1H NMR (400 MHz, DMSO) δ 10.17 (s, 1H), 8.73 (dd, J=8.2, 4.8 Hz, 1H), 7.99-7.88 (m, 2H), 7.72 (dd, J=7.1, 1.1 Hz, 1H), 7.58-7.49 (m, 4H), 5.83 (s, 1H), 4.14 (s, 1H).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe solvent is removed in vacuo
  3. customthe precipitate is collected in a Buchner funnel

Sources & evidence

ORD record
ord-0802724e0fa44ed2bb5da7a330fffd00
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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