Diisopropylethylamine → HCID 178463579, compound

HRID 1429827Notes

Reaction equation

HRID 1429827 reaction equation
[NH2:1][CH:2]([C:4]1[N:5]=[C:6]2[S:19][CH:18]=[CH:17][N:7]2[C:8](=[O:16])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:3].Br[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][NH:25]2.C(N(CC)C(C)C)(C)C>C(O)C>[C:10]1([C:9]2[C:8](=[O:16])[N:7]3[CH:17]=[CH:18][S:19][C:6]3=[N:5][C:4]=2[CH:2]([NH:1][C:21]2[N:29]=[CH:28][N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][NH:25]3)[CH3:3])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581114357-(1-aminoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 178419477HCID 178419477, compound

Product 1

HCID 178463579HCID 178463579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-(1-aminoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.025 g, 0.092 mmol), 6-bromo-9H-purine (0.033 g, 0.16 mmol), and N,N-diisopropylethylamine (0.029 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 C19H16N7OS (M+H)+: m/z=390.1. Found: 390.1. 1H NMR (DMSO-d6, 400 MHz) δ 8.08 (1H, s), 8.06 (1H, s), 7.97 (1H, d, J=4.8 Hz), 7.51 (1H, d, J=4.8 Hz), 7.44˜7.33 (6H, m), 5.15 (1H, m), 1.29 (3H, d, J=7.2 Hz) ppm.

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-48eaa207051e491d9f811d46c5ee50a8
Source dataset
uspto-grants-2015_01
Patent number
US08940752B2

Reaction notes

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