Sodium Bicarbonate → HCID 15616694, compound

HRID 973410Notes

Reaction equation

HRID 973410 reaction equation
[Br:1][C:2]1[N:6]2[C:7]([CH3:15])=[C:8]([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[N:10][C:5]2=[N:4][C:3]=1[C:16](=[O:27])[C:17]#[C:18][CH2:19][O:20]C1CCCCO1.C(=O)(O)[O-].[Na+]>CO.Cl>[Br:1][C:2]1[N:6]2[C:7]([CH3:15])=[C:8]([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[N:10][C:5]2=[N:4][C:3]=1[C:16](=[O:27])[C:17]#[C:18][CH2:19][OH:20]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 19989901HCID 19989901, compound

Product 1

HCID 15616694HCID 15616694, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 5.0 g (11.5 mmol) of 1-(3-bromo-6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl)-4-(tetrahydropyran-2-yloxy)-2-butyn-1-one in a mixture of 100 ml of methanol and 35 ml of 2N hydrochloric acid stood at room temperature for 30 minutes and then was neutralized with aqueous sodium bicarbonate. Extraction with chloroform gave an oil which was chromatographed over silica (chloroform: ether: methanol 100:0:0 gradually changing to 0:95:5) to obtain 1.3 g (32%) of 1-(3-bromo-6-ethyl-7-methoxy-5-methylimidazo [1,2-a]pyrimidin-2-yl)-4-hydroxy-2-butyn-1-one as off-white crystals melting at 212°-3° C. (decomp.).

Workup

  1. extractionExtraction with chloroform
  2. customgave an oil which
  3. customwas chromatographed over silica (chloroform: ether: methanol 100:0:0

Sources & evidence

ORD record
ord-f23cbc1cd8d94a6bb9bec894ce030799
Source dataset
uspto-grants-1991_11
Patent number
US05063229

Reaction notes

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