Potassium Carbonate → HCID 136409088, compound

HRID 571624Notes

Reaction equation

HRID 571624 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

5

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 67994427HCID 67994427, compoundHCID 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

Workup

  1. customIt was evaporated in high vacuum
  2. dissolutionthe residue dissolved in water methanol mixture
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-9ef255663a9447fd87680d42a5293301
Source dataset
uspto-grants-2015_05
Patent number
US09029344B2

Reaction notes

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