Acetic Acid → HCID 67212082, compound

HRID 2036349Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]=O)[CH2:2]1.[NH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]([O:22][CH3:23])=[N:20][C:19]2[C:14]1=[N:15][C:16]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[N:17][C:18]=2[NH2:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:26]([O:25][C:16]1[N:15]=[C:14]2[C:19]([N:20]=[C:21]([O:22][CH3:23])[N:13]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:7][CH:3]2[CH2:4][CH2:5][CH2:6][O:1][CH2:2]2)=[C:18]([NH2:24])[N:17]=1)[CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 20 °C

Procedure

Tetrahydro-2H-pyran-3-carbaldehyde (19.39 mg, 0.17 mmol) was added to 9-(3-aminopropyl)-2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine (50 mg, 0.17 mmol) in DCM (1 ml). Sodium triacetoxyborohydride (72.0 mg, 0.34 mmol) and DCM (1 ml) was added followed by acetic acid (0.024 ml, 0.425 mmol). The mixture was stirred at 20° C. under nitrogen for 5 hours. The mixture was quenched with NaHCO3 (5 ml) and diluted with DCM (2 ml). The organic layer was separated using a hydrophobic frit and the solvent removed in vacuo. The sample was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen to give the title compound as white solid (47 mg).

Workup

customThe mixture was quenched with NaHCO3 (5 ml)
additiondiluted with DCM (2 ml)
customThe organic layer was separated
customthe solvent removed in vacuo
dissolutionThe sample was dissolved in 1:1 MeOH
customDMSO (1 ml) and purified by Mass Directed AutoPrep (Method A)
customThe solvent was dried under a stream of nitrogen

Sources & evidence

ORD record: ord-f97c761cdf204445a8c0c0141f8779d6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575181B2

Reaction notes

Loading…