Isonicotinic Acid → HCID 178522388, compound

HRID 1470729Notes

Reaction equation

HRID 1470729 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:22][C:23]1[C:24]([OH:30])=[N:25][C:26]([Cl:29])=[N:27][CH:28]=1>CN(C=O)C>[Cl:29][C:26]1[N:25]=[C:24]([OH:30])[C:23]([NH:22][C:1](=[O:9])[C:2]2[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=2)=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 178508024HCID 178508024, compound

Product 1

HCID 178522388HCID 178522388, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.88 g (47.7 mmol) isonicotinic acid and 7.74 g (47.7 mmol) 1,1′-carbonyldiimidazole in 30 mL DMF are stirred for 30 min at 45° C. prior to addition of 8.0 g (47.7 mmol) of 5-amino-2-chloro-pyrimidin-4-ol. The mixture is stirred for 12 h at rt, concentrated and purified by HPLC (reversed phase, water (+0.1% TFA)/MeOH) to yield N-(2-chloro-4-hydroxy-pyrimidin-5-yl)-isonicotinamide.

Workup

  1. concentrationconcentrated
  2. custompurified by HPLC (reversed phase, water (+0.1% TFA)/MeOH)

Sources & evidence

ORD record
ord-2190c54b3ae0458cb5182b03b416a358
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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