Hydrochloric Acid → 2-morpholin-4-yl-6-piperidin-4-yl-1H-pyrimidin-4-one;hydrochloride

HRID 1526469Notes

Reaction equation

HRID 1526469 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[C:18]([OH:20])[N:17]=[C:16]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:27]>C(OCC)C>[ClH:27].[N:21]1([C:16]2[N:17]=[C:18]([OH:20])[CH:19]=[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451771HCID 178451771, compound

Product 1

HCID 1784796222-morpholin-4-yl-6-piperidin-4-yl-1H-pyrimidin-4-one;hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(6-Hydroxy-2-morpholin-4-ylpyrimidin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.19 g, 0.52 mmol) was added to 2 N hydrogen chloride in diethyl ether and stirred for 18 hours at room temperature. The resultant product was isolated by filtration and washed with ether to provide 2-morpholin-4-yl-6-piperidin-4-yl-pyrimidin-4-01, hydrochloride salt (0.16 g, 91% yield) as a white solid. 1H NMR (300 MHz, CD3OD/TMS): δ=6.17 (s, 1H), 3.90-3.78 (m, 8H), 3.60-3.50 (m, 2H), 3.26-3.1 (m, 3H), 2.32-2.20 (m, 2H), 2.00-1.80 (m, 2H). 13C NMR (75 MHz, CD3OD/TMS): δ=171.60, 164.86, 155.10, 97.63, 66.93, 45.13, 46.92, 44.81, 38.29, 28.41.

Sources & evidence

ORD record
ord-bc334e0e5ebd4a92a7d78dcedf8db572
Source dataset
uspto-grants-2015_07
Patent number
US09085585B2

Reaction notes

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