HCID 25223691, compound → HCID 135723756, compound

HRID 533206Notes

Reaction equation

C(OC[N:10]1[C:18]2[C:17]([O:19]C)=[N:16][CH:15]=[N:14][C:13]=2[C:12]([CH2:21][N:22]([CH2:26][C@@H:27]2[CH2:31][O:30]C(C)(C)[O:28]2)[CH2:23][CH2:24][OH:25])=[CH:11]1)C1C=CC=CC=1>Cl>[OH:28][C@@H:27]([CH2:31][OH:30])[CH2:26][N:22]([CH2:21][C:12]1[C:13]2[N:14]=[CH:15][NH:16][C:17](=[O:19])[C:18]=2[NH:10][CH:11]=1)[CH2:23][CH2:24][OH:25]

Participants

Conditions

Temperature: 100 °C

Procedure

The product from Example 13.2 (0.165 g, 0.361 mmol) was dissolved in 37% HCl (4 ml) and heated to 100° C. for 1.5 h. The solvent was evaporated and the residue dissolved in MeOH and a little water and neutralized with Amberlyst A21 resin. The mixture was filtered and the solvent was evaporated. The residue was chromatographed on silica gel (iPrOH—H2O-28% NH4OH 9:0.5:0.5 then 8:1.5:0.5) to give (R)-7-(((2,3-dihydroxypropyl)(2-hydroxyethyl)amino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (0.074 g, 72.5%) as a colourless solid. [α]D20 +18.4 (c, 0.56, H2O). 1H NMR (D2O+NaOD, referenced to internal acetonitrile at 2.06 ppm) δ 8.07 (s, 1H), 7.35 (s, 1H), 3.94-3.65 (m, 3H), 3.68 (t, J=6.2 Hz, 2H), 3.50 (dd, J=11.7, 4.2 Hz, 1H), 3.40 (dd, J=11.6, 6.2 Hz, 1H), 2.75-2.48 (m, 4H). 13C NMR (D2O, 75.5 MHz, referenced to internal acetone at 31.5 ppm) δ 156.3, 145.4, 143.7, 132.0, 118.6, 109.2, 68.9, 65.1, 58.5, 56.7, 56.3, 48.8. +ESMS Found 283.1398 C12H19N4O4 (M+H)+ requires 283.1406.

Workup

customThe solvent was evaporated
dissolutionthe residue dissolved in MeOH
filtrationThe mixture was filtered
customthe solvent was evaporated
customThe residue was chromatographed on silica gel (iPrOH—H2O-28% NH4OH 9:0.5:0.5

Sources & evidence

ORD record: ord-58eebc29f2554a21af7c7e7e7ae5374f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853224B2

Reaction notes

Loading…