Hydrochloric Acid → N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-(4-amino-phenyl)-acetamide, hydrochloride salt

HRID 858040Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:38])[NH:16][C:17]2[C:18](=[O:37])[N:19]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[C:20](=[O:28])[N:21]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[C:22]=2[NH2:23])=[CH:10][CH:9]=1)(C)(C)C.[ClH:40]>O1CCOCC1>[ClH:40].[NH2:23][C:22]1[N:21]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:20](=[O:28])[N:19]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])[C:18](=[O:37])[C:17]=1[NH:16][C:15](=[O:38])[CH2:14][C:11]1[CH:10]=[CH:9][C:8]([NH2:7])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (4-{[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester (2.20 g, 4.10 mmol) in a solution of a 4.0N aqueous hydrochloric acid solution in dioxane (37.0 mL) was stirred at 25° C. for 1 h. A suspension formed during this time. The reaction mixture was cooled to 0° C. The resulting solid was collected by filtration, washed with dioxane and cold diethyl ether, and dried in vacuo to afford N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-(4-amino-phenyl)-acetamide, hydrochloride salt (1.73 g, 89%); LRMS for C23H23FN5O3 (M+H)+ at m/z=438.

Workup

customA suspension formed during this time
filtrationThe resulting solid was collected by filtration
washwashed with dioxane and cold diethyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-8191b6e7e4574d1bb6f7f86672bad074
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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