Acetic Acid → HCID 10112525, compound

HRID 750542Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[C:10]2[N:11]=[C:12]([NH2:20])[N:13]=[C:14]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[C:9]=2[N:8]=[N:7]1.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1COCC1>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[CH2:5][N:6]2[C:10]3[N:11]=[C:12]([NH2:20])[N:13]=[C:14]([C:15]4[O:16][CH:17]=[CH:18][CH:19]=4)[C:9]=3[N:8]=[N:7]2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 3-(3-aminobenzyl)-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (200 mg, 0.65 mmol) and 4A molecular sieves in THF (10 mL) was treated with 4-fluorobenzaldehyde (0.04 mL, 0.37 mmol), heated to 40° C. for 3 h, cooled to room temperature, treated sodium triacetoxyborohydride (400 mg, 1.89 mmol) and acetic acid (0.1 mL) and stirred for 15 minutes. The reaction was quenched by addition of sat. NaHCO3 (5 mL), extracted with EtOAc (2×5 mL) and the combined organic phase dried (MgSO4), concentrated in vacuo and purified by chromatography [(SiO2; EtOAc:Heptane (1:2)] to give the title compound (60 mg, 44%) as a white solid.

Workup

temperaturecooled to room temperature
customThe reaction was quenched by addition of sat. NaHCO3 (5 mL)
extractionextracted with EtOAc (2×5 mL)
dry with materialthe combined organic phase dried (MgSO4)
concentrationconcentrated in vacuo
custompurified by chromatography [(SiO2

Sources & evidence

ORD record: ord-18833adcf5464c438ba3225399c00c31
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405219B2

Reaction notes

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