Guanidine Hydrochloride → 2-Amino-6-cyclopentylpyrimidin-4-OL

HRID 2360567Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][C:6]([CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=O)C.Cl.[NH2:15][C:16]([NH2:18])=[NH:17].CC(C)([O-])C.[K+]>CO>[NH2:17][C:16]1[NH:18][C:4](=[O:3])[CH:5]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-cyclopentyl-3-oxo-propionic acid ethyl ester (5.0 g, 27.4 mmol) and guanidine hydrochloride (3.1 g, 33.0 mmol) in MeOH (50 mL) at 23° C. was added potassium tert-butoxide, portionwise (16.7 g. 149 mmol) over 15 min with vigorous stirring and the reaction warmed to 60° C. The reaction was cooled to room temperature (rt) and stirred overnight and the precipitated salt was removed by filtration. The solution was concentrated to approximately 10 mL then diluted with 10 mL of water and adjusted to pH=5 by the addition of 6.0 N HCl (6.1 mL). The resulting precipitate was filtered and dried via suction then vacuum to yield a white solid (4.3 g, 87%) that was used without further purification. 1H NMR (MeOD): 10.71-10.54 (m, 1H), 6.58-6.32 (m, 2H), 5.44-5.37 (m, 1H), 2.66 (p, J=8.1, 1H), 1.91-1.73 (m, 2H), 1.72-1.48 (m, 6H).

Workup

temperatureThe reaction was cooled to room temperature (rt)
stirringstirred overnight
customthe precipitated salt was removed by filtration
concentrationThe solution was concentrated to approximately 10 mL
additionthen diluted with 10 mL of water
additionadjusted to pH=5 by the addition of 6.0 N HCl (6.1 mL)
filtrationThe resulting precipitate was filtered
customdried via suction

Sources & evidence

ORD record: ord-80b320f26f5f4e82815b6d9138988aa7
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686142B2

Reaction notes

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