Diisopropylethylamine → HCID 178431861, compound

HRID 58256Notes

Reaction equation

HRID 58256 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[NH2:11][CH:12]([C:14]1[N:15]=[C:16]2[S:29][CH:28]=[C:27]([CH3:30])[N:17]2[C:18](=[O:26])[C:19]=1[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)C>[CH3:30][C:27]1[N:17]2[C:18](=[O:26])[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:14]([CH:12]([NH:11][C:2]3[N:10]=[CH:9][N:8]=[C:7]4[C:3]=3[N:4]=[CH:5][NH:6]4)[CH3:13])[N:15]=[C:16]2[S:29][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581114147-(1-aminoethyl)-3-methyl-6-pyridin-4-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 178419477HCID 178419477, compound

Product 1

HCID 178431861HCID 178431861, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.064 g, 0.32 mmol), 7-(1-aminoethyl)-3-methyl-6-pyridin-4-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.046 g, 0.16 mmol), and N,N-diisopropylethylamine (0.056 mL, 0.32 mmol) in ethanol (0.5 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resultant residue was purified on RP-HPLC (XBridge C18 Column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH) to give the product as the free base. LCMS calculated for C19H17N8OS (M+H)+: m/z=405.1. Found: 405.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. customthe resultant residue was purified on RP-HPLC (XBridge C18 Column
  5. washeluting with a gradient of acetonitrile/water containing 0.15% NH4OH)
  6. customto give the product as the free base

Sources & evidence

ORD record
ord-a8466ab727434df4ba6107e6e03447d3
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

Loading…