Hydrochloric Acid → HCID 22674267, compound

HRID 1005979Notes

Reaction equation

HRID 1005979 reaction equation
C([O:3][C:4]([C:6]1[C:7]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])=[N:8][C:9]([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:10][CH:11]=1)=[O:5])C.Cl>C(O)C>[C:20]1([CH3:25])[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]([C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:17]=2)[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69924331HCID 69924331, compound

Product 1

HCID 22674267HCID 22674267, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.33 g (0.98 mmol) 4-o-tolyloxy-[2,2′]bipyrimidinyl-5-carboxylic acid ethyl ester in 15 ml ethanol 3.68 ml 0.4 N NaOH was added and the resulting solution was stirred for 2 hrs at RT. The pH of the solution was adjusted to 4 with 1N HCl. The aqueous solution was extracted three times with CH2Cl2. The combined organic phases were dried (Na2SO4), filtered and evaporated. The resulting solid was triturated twice with diethyl ether, filtered off and dried to give 0.26 g (85%) 4-o-tolyloxy-[2,2′]bipyrimidinyl-5-carboxylic acid as a light yellow solid, MS (ISN): 307.3 (M−H)−.

Workup

  1. extractionThe aqueous solution was extracted three times with CH2Cl2
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting solid was triturated twice with diethyl ether
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-e6c3d11d9b354d3a9b98b0ce29802612
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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