HCID 53944659, compound → 2-(Morpholin-4-yl)pyrimidine-5-carboxylic acid

HRID 1907707Notes

Reaction equation

HRID 1907707 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]([O:15]CC)=[O:14])=[CH:9][N:8]=2)[CH2:3][CH2:2]1>Cl.O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 53944659HCID 53944659, compound

Product 1

HCID 31609792-(Morpholin-4-yl)pyrimidine-5-carboxylic acidYield 107.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of ester 122 (0.205 g, 0.86 mmol) in 2N HCl in H2O (10 mL) was stirred at 110° C. in a pressure vessel for 6 h, cooled to −78° C. and lyophilized for 2 days. The resulting amorphous solid was further dried using a mixture of dry acetonitrile (10 mL) and dry benzene (10 mL) followed by concentration (this was repeated 3 times) to give compound 123 (0.193 g, 92% yield). LRMS: 209.1 (calc) 210.0 (obs).

Workup

  1. customThe resulting amorphous solid was further dried
  2. additiona mixture of dry acetonitrile (10 mL) and dry benzene (10 mL)
  3. concentrationfollowed by concentration (

Sources & evidence

ORD record
ord-6e224ce6bbbc4b14ae7d568535675e76
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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