Methanol → HCID 178482932, compound

HRID 869680Notes

Reaction equation

HRID 869680 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]([NH:17][C:18](=[O:25])[CH2:19][C:20](OCC)=[O:21])[NH:14][N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:26]O.C(O[CH2:32][CH3:33])(=O)C>CN(C)C1C=CN=CC=1.O>[CH3:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]3[N:17]=[C:18]([OH:25])[CH:19]=[C:20]([OH:21])[N:14]3[N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:26][N:17]([C:15]1[CH:16]=[CH:12][N:13]=[CH:32][CH:33]=1)[CH3:18]

Participants

6

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 178472229HCID 178472229, compound

Product 1

HCID 178482932HCID 178482932, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

Method B (DMAP salt): A suspension of ethyl 3-{[3-(3-methylquinoxalin-2-yl)-1H-pyrazol-5-yl]amino}-3-oxopropanoate (1.00 g, 2.95 mmol) and 4-dimethylaminopyridine (DMAP) (1.08 g, 8.84 mmol) in water (7 mL), tetrahydrofuan (7 mL), and methanol (7 mL) was heated at 65° C. for 4 h. After being cooled to ambient temperature, the reaction mixture was diluted with water and ethyl acetate. The aqueous layer was collected and concentrated in vacuo. The residue was triturated with ether acetate to give 2-(3-methylquinoxalin-2-yl)pyrazolo[1,5-a]pyrimidine-5,7-diol DMAP salt. MS (APCI): m/z 294 (M+H).

Workup

  1. temperatureAfter being cooled to ambient temperature
  2. customThe aqueous layer was collected
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with ether acetate

Sources & evidence

ORD record
ord-4175ad4f23c943c39e5158ff4d41510b
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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