Hydrochloric Acid → 2-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetic acid hydrochloride

HRID 445056Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[C:4]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:3]=1.[ClH:26].C(OC(C)C)(=O)C>C(#N)C>[ClH:26].[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)=[C:4]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of the product from step (v) (8.00 g, 23.4 mmol) in acetonitrile (48.0 g) was heated to 40° C., and 35% aq. HCl (2.68 g, 25.7 mmol) was slowly added to the suspension. After the mixture was stirred at 40° C. for 1 hour, isopropyl acetate (160 g) was slowly added to the mixture. The mixture was cooled to 15° C. and stirred for 1 hour. The resulting precipitate was collected by filtration, washed with combined solution of acetonitrile (5.14 g) and isopropyl acetate (13.9 g), and dried to give the subtitle compound as a white solid, 8.27 g.

Workup

temperatureThe mixture was cooled to 15° C.
stirringstirred for 1 hour
filtrationThe resulting precipitate was collected by filtration
washwashed with combined solution of acetonitrile (5.14 g) and isopropyl acetate (13.9 g)
customdried

Sources & evidence

ORD record: ord-15a02acb226f415fa29897ee698a9412
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476288B2

Reaction notes

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