Actarit → 2-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide

HRID 720622

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[NH2:27][C:28]1[C:29](=[O:40])[NH:30][C:31](=[O:39])[N:32]([CH2:35][CH2:36][CH2:37][CH3:38])[C:33]=1[NH2:34]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([NH:27][C:28]2[C:29](=[O:40])[NH:30][C:31](=[O:39])[N:32]([CH2:35][CH2:36][CH2:37][CH3:38])[C:33]=2[NH2:34])=[O:14])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (4-acetylamino-phenyl)-acetic acid (348 mg, 1.65 mmol) in N,N-dimethylformamide (2.5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (316 mg, 1.80 mmol). The resulting mixture was stirred at 25° C. for 20 min. At this time, the reaction was treated with 5,6-diamino-1-butyl-1H-pyrimidine-2,4-dione (300 mg, 1.5 mmol) followed by 4-dimethylaminopyridine (37 mg, 0.3 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (5.0 mL) and was brought to pH=5 with a 1N aqueous hydrochloric acid solution. The resulting solid was collected by filtration, washed with water, and dried in vacuo to afford 2-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide (330 mg, 59%) as a light tan solid: LR-MS for C18H23N5O4 (M+H)+ at m/z=374

Workup

stirringThe reaction was stirred at 25° C. for 18 h
concentrationAt this time, the reaction was concentrated in vacuo
additionThe residue was diluted with water (5.0 mL)
filtrationThe resulting solid was collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-d8cf9b142d7845dfa56e6df71743aad3
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135475B2

Linked notes

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