Diisopropylethylamine → HCID 178463580, compound

HRID 58279Notes

Reaction equation

HRID 58279 reaction equation
[NH2:1][CH:2]([C:4]1[N:5]=[C:6]2[S:20][CH:19]=[CH:18][N:7]2[C:8](=[O:17])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[CH3:3].Br[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[N:24]=[CH:25][NH:26]2.C(N(CC)C(C)C)(C)C>C(O)C>[F:16][C:12]1[CH:11]=[C:10]([C:9]2[C:8](=[O:17])[N:7]3[CH:18]=[CH:19][S:20][C:6]3=[N:5][C:4]=2[CH:2]([NH:1][C:22]2[N:30]=[CH:29][N:28]=[C:27]3[C:23]=2[N:24]=[CH:25][NH:26]3)[CH3:3])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581113987-(1-aminoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 178419477HCID 178419477, compound

Product 1

HCID 178463580HCID 178463580, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-(1-aminoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.025 g, 0.086 mmol), 6-bromo-9H-purine (0.031 g, 0.16 mmol), and N,N-diisopropylethylamine (0.027 mL, 0.16 mmol) in ethanol (0.5 mL) was heated at 110° C. overnight. The mixture was filtered and the filtrate was purified on preparative-LCMS (XBridge C18 Column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH) to give the desired product. LCMS calculated for C19H15FN7OS (M+H)+: m/z=408.1. Found: 408.0.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified on preparative-LCMS (XBridge C18 Column
  3. washeluting with a gradient of acetonitrile/water containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-297bc9cb9a7e4499813d32334c41c60e
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

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