Bromoacetic Acid → HCID 57988785, compound

HRID 889051Notes

Reaction equation

[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:22]3[CH:23]=[N:24][NH:25][CH:26]=3)=[N:8][C:7]=2[N:6]([CH2:27][CH2:28][CH3:29])[C:5]1=[O:30])[CH2:2][CH3:3].Br[CH2:32][C:33]([OH:35])=[O:34].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[O:30]=[C:5]1[N:6]([CH2:27][CH2:28][CH3:29])[C:7]2[N:8]=[C:9]([C:22]3[CH:26]=[N:25][N:24]([CH2:32][C:33]([OH:35])=[O:34])[CH:23]=3)[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:21])[CH3:19])[C:11]=2[C:12](=[O:13])[N:4]1[CH2:1][CH2:2][CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of solution of 1,3-dipropyl-8-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (600 mg, 1.38 mmol), bromo acetic acid (289 mg, 2.08 mmol) and K2CO3 (575 mg, 4.16 mmol) in acetone (10 ml) was heated at 80° C. for 3 hrs. The reaction mixture was filtered through celite and washed with acetone. The organic layer was concentrated and the residue obtained was purified by column chromatography to obtain {4-[2,6-dioxo-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-pyrazol-1-yl}-acetic acid (420 mg, 61%) as white solid.

Workup

filtrationThe reaction mixture was filtered through celite
washwashed with acetone
concentrationThe organic layer was concentrated
customthe residue obtained
customwas purified by column chromatography

Sources & evidence

ORD record: ord-3d2e91d906f94842ba50abeaf483cd6e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252797B2

Reaction notes

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