Sulfuric Acid → HCID 15158140, compound

HRID 703986Notes

Reaction equation

HRID 703986 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:24].N([O-])=O.[Na+]>O>[O:24]=[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][NH:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15158121HCID 15158121, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15158140HCID 15158140, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-(2-aminopyrimidin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.70 g) and 50% sulfuric acid (5.6 ml) was gradually added aqueous solution (5.6 ml) of sodium nitrite (1.68 g) at 5° to 10° C., and the resultant mixture was stirred for 3 hours at the same temperature and then for 2 hours at room temperature. To the reaction mixture was added water (14 ml). The precipitates were collected by filtration subjected to a column chromatography on silica gel (14 g) with a mixture of chloroform and methanol (10:1) as an eluent. The fractions containing the objective compound were combined and the solvent was evaporated in vacuo to give 3-(2-oxo-1,2-dihydropyrimidin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.44 g).

Workup

  1. customat 5° to 10° C.
  2. filtrationThe precipitates were collected by filtration
  3. additionsubjected to a column chromatography on silica gel (14 g) with a mixture of chloroform and methanol (10:1) as an eluent
  4. additionThe fractions containing the objective compound
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ad84100273b54363a4ac53bcef04321d
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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