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

HRID 445055Notes

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](CC#N)=[CH:12][CH:11]=2)=[C:4]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:3]=1.[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28]>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:28][C:27]([OH:25])=[O:29])=[CH:12][CH:11]=2)=[C:4]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The suspension of the wet product from step (iv) (5.90 g) in 10% aq.NaOH (34.2 g) and ethanol (24.9 g) was heated at 85° C. for 5 hours. The mixture was cooled to 25° C., and the pH of the solution was adjusted to pH 6.5 with 18% aq. acetic acid (31.1 g). The resulting precipitate was collected by filtration, washed with water (18.6 g) and acetonitrile (15.5 g) respectively, and dried to give the subtitle compound as a white solid, 4.43 g.

Workup

filtrationThe resulting precipitate was collected by filtration
washwashed with water (18.6 g) and acetonitrile (15.5 g) respectively
customdried

Sources & evidence

ORD record: ord-3c2867d534f24240b31bc8c806790b18
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476288B2

Reaction notes

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