Formaldehyde → 7-(((2RS,3SR)-1,3,4-trihydroxybutan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

HRID 533211Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:8][O:7]C(C)(C)[O:5][CH2:4][C@H:3]1[OH:11].[CH:12]1[C:16]2[N:17]=[CH:18][NH:19][C:20](=[O:21])[C:15]=2[NH:14][CH:13]=1.[CH2:22]=O>O>[OH:7][CH2:8][CH:2]([NH:1][CH2:22][C:12]1[C:16]2[N:17]=[CH:18][NH:19][C:20](=[O:21])[C:15]=2[NH:14][CH:13]=1)[CH:3]([OH:11])[CH2:4][OH:5]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol (155 mg, 0.96 mmol), 9-deazahypoxanthine (100 mg, 0.74 mmol) and 37% aq formaldehyde (140 μl, 1.85 mmol) in water (2 ml) was stirred and heated in stoppered flask at 85° C. overnight. The solution was evaporated to dryness. The residue was stirred in methanolic ammonia for 10 minutes and then evaporated. The residue was chromatographed on silica (DCM-MeOH-cNH3 6:3.5:0.5) to give the racemic 7-(((2RS,3SR)-1,3,4-trihydroxybutan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (55 mg, 0.20 mmol, 30% yield) as a white solid 1H NMR (CDCl3) 2.76 (1H, q, J 5.2 Hz), 3.48 (1H, dd, J 6.3, 11.9 Hz), 3.60 (2H, m), 3.70 (2H, m), 3.85 (2H, ABq), 7.34 (1H, s), 7.78 (1H, s). 13C NMR (CDCl3) δ0.2, 59.8, 59.8, 63.5, 71.2, 113.1, 117.5, 129.2, 142.4, 143.5, 155.4. m/z (ESI+) 537 (2MH+, 20%), 269 (MH+, 100%). HRMS (ESI+) C11H16N4O4 requires 269.1241. found 269.1250.

Workup

customThe solution was evaporated to dryness
stirringThe residue was stirred in methanolic ammonia for 10 minutes
customevaporated
customThe residue was chromatographed on silica (DCM-MeOH-cNH3 6:3.5:0.5)

Sources & evidence

ORD record: ord-efabb7a3f7d94350b9bbf38e43efa91d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853224B2

Reaction notes

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