Diisopropylethylamine → HCID 178431858, compound

HRID 58246Notes

Reaction equation

HRID 58246 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][CH:23]=[CH:22][N: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][CH:23]=[CH:22][N: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 668636747-(1-aminoethyl)-3-methyl-6-pyridin-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 178419477HCID 178419477, compound

Product 1

HCID 178431858HCID 178431858, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (9.300 mg, 0.004673 mmol), 7-(1-aminoethyl)-3-methyl-6-pyridin-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (11 mg, 0.039 mmol), and N,N-diisopropylethylamine (8.152 μL, 0.004680 mmol) in ethanol (0.3 mL) was refluxed under nitrogen overnight. The mixture was concentrated under reduced pressure and the residue was purified on RP-HPLC (eluting with a gradient of methanol/water containing 1% TFA) to provide the product as a TFA salt. LCMS calculated for C19H17N8OS (M+H)+: m/z=405.1. Found: 405.3.

Workup

  1. temperaturewas refluxed under nitrogen overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified on RP-HPLC (
  4. washeluting with a gradient of methanol/water containing 1% TFA)

Sources & evidence

ORD record
ord-c0ed97ccc0124494beccdfde4fdcfc99
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

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