Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde → HCID 59213122, compound

HRID 2244099Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[N:6]=[C:5]2[N:13]([CH3:15])[CH3:14].C[O:17][CH:18]1[CH:22]([CH:23]=O)[CH2:21][CH:20](OC)O1>CC(O)=O>[CH3:14][N:13]([CH3:15])[C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[C:7]([N:12]2[CH:20]=[CH:21][C:22]([CH:18]=[O:17])=[CH:23]2)[N:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirring mixture of 6-fluoro-N4,N4-dimethylquinazoline-2,4-diamine (20.0 mg, 0.10 mmol), 2,5-dimethyoxy-3-tetrahydrofurancarboxaldehyde (43 μL, 0.30 mmol), and AcOH (500 μL) was heated at 90° C. for 30 minutes. The mixture was evaporated to dryness and the obtained residue was purified via silica gel chromatography using 70% hexanes/30% EtOAc to obtain the desired aldehyde as a white solid (15 mg, 0.05 mmol, 50% yield). LC/MS (10-99%) M/Z 285.1 retention time 3.23 min.

Workup

customThe mixture was evaporated to dryness
customthe obtained residue was purified via silica gel chromatography

Sources & evidence

ORD record: ord-86dbb146039849adbe2f3e0589c5a0d8
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678802B2

Reaction notes

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