Ethanolamine → HCID 135858821, compound

HRID 533196Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].[CH:5]1[C:9]2[N:10]=[CH:11][NH:12][C:13](=[O:14])[C:8]=2[NH:7][CH:6]=1.[CH2:15]=O>O>[OH:2][CH2:1][CH2:3][NH:4][CH2:15][C:5]1[C:9]2[N:10]=[CH:11][NH:12][C:13](=[O:14])[C:8]=2[NH:7][CH:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of ethanolamine (78 μl, 0.96 mmol), 9-deazahypoxanthine (100 mg, 0.74 mmol) and 37% aq formaldehyde (72 μl, 0.96 mmol) in water (5 ml) was stirred and heated in stoppered flask at 85° C. overnight. The solution was evaporated to dryness and the residue was chromatographed on silica (DCM-MeOH-cNH3 6:3.5:0.5) to give 7-((2-hydroxyethylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (100 mg, 0.48 mmol, 65% yield) as a pale brown solid. 1H NMR (300 MHz, CD3OD) 2.80 (2H, t, J 5.5 Hz), 3.68 (2H, t, J 5.5 Hz), 3.97 (2H, s), 7.42 (1H, s), 7.88 (1H, s); 13C NMR (75 MHz, MeOD+DCl) 42.0, 50.7, 58.43, 105.2, 120.5, 133.8, 135.0, 147.1, 153.0

Workup

customThe solution was evaporated to dryness
customthe residue was chromatographed on silica (DCM-MeOH-cNH3 6:3.5:0.5)

Sources & evidence

ORD record: ord-287bb858d254474e944c4b00cf7de96d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853224B2

Reaction notes

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