Potassium Carbonate → HCID 136409088, compound

Reaction equation

NCC[CH:4]([S:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH:5]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([N:12]2[CH:20]=[N:19][C:18]3[C:13]2=[N:14][CH:15]=[N:16][C:17]=3[NH2:21])[O:6]1.C(=O)([O-])[O-].[K+].[K+].[NH2:35][C:36]1[NH:45][C:44](=[O:46])[C:43]2[C:38](=[N:39][CH:40]=[C:41]([CH2:47]Br)[N:42]=2)[N:37]=1.[CH3:49][C:50]([N:52](C)C)=O>>[NH2:35][C:36]1[NH:45][C:44](=[O:46])[C:43]2[C:38](=[N:39][CH:40]=[C:41]([CH2:47][NH:52][CH2:50][CH2:49][N:26]3[CH2:27][CH2:28][CH:23]([S:22][CH2:4][CH:5]4[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([N:12]5[CH:20]=[N:19][C:18]6[C:13]5=[N:14][CH:15]=[N:16][C:17]=6[NH2:21])[O:6]4)[CH2:24][CH2:25]3)[N:42]=2)[N:37]=1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 31374Dimethylacetamide

HCID 67994427HCID 67994427, compound

HCID 135818758HCID 135818758, compound

Product 1

HCID 136409088HCID 136409088, compoundYield 50%

Procedure

To a solution of 2-[1-(2-Amino-ethyl)-piperidin-4-ylsulfanylmethyl]-5-(6-amino-purin-9-yl)-tetrahydro-furan-3,4-diol (100.0 mg, 0.244 mmol, 1 eq) (8) and potassium carbonate (337.9 mg, 2.44 mmol, 10 eq) in 20 mL dimethylacetamide, 2-amino-6-bromomethyl-3H-pteridin-4-one (87.0 mg, 0.244 mmol, 1 eq) (11) was added and then stirred at room temperature for 24 hours. It was evaporated in high vacuum and the residue dissolved in water methanol mixture and purified by HPLC to give compound 13 (71.0 mg, 0.122 mmol, 50%) of a yellowish powder. MS (ESI) calculated for C24H32N12O4S [M+H]+ 585.24, found 585.1