Hydrochloric Acid → HCID 136337780, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-((5-(benzyloxymethyl)-4-tert-butoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(methylthiomethyl)propane-1,3-diol (200 mg, 0.421 mmol) in methanol (1 mL) was added to a solution of concentrated hydrochloric acid (2 mL) in methanol (5 mL) and the reaction was heated at 100° C. for 3 h. The contents of the flask were concentrated under reduced pressure, redissolved in methanol (5 mL) and Amberlyst 21 resin (˜1 g) was added. After stirring for 1 h at ambient temperature the resin was removed by filtration, the filtrate concentrated under reduced pressure and then redissolved in 7 M methanolic ammonia (5 mL) and stirred for 30 min. TLC(CH2Cl2:7 M methanolic ammonia, 4:1, visualised with Erlichs) indicated the reaction was complete so the solution was concentrated under reduced pressure and the residue dry-loaded on to a silica column. Purification by flash column chromatography (CH2Cl2:7 M methanolic ammonia, 3:1, visualised with Erlichs) gave 7-((1,3-dihydroxy-2-(methylthiomethyl)propan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (62.0 mg, 49%) as a white foam. 1H NMR (D2O, drop of DCl) δ 8.91 (1H), 7.79 (1H), 4.43 (2H), 3.84 (d, J=12.7 Hz, 2H), 3.79 (d, J=12.7 Hz, 2H), 2.92 (s, 2H), 2.13 (s, 3H). 13C NMR (D2O, drop of DCl): δ 152.8, 145.2, 133.3, 131.8, 118.5, 103.5, 67.4, 59.2, 35.4, 33.5, 17.0. +ESMS Found 299.1185 (M+Fr) C12H19N4O3S requires 299.1178.

Provenance & Evidence