Diisopropylethylamine → HCID 178463609, compound

HRID 58278Notes

Reaction equation

HRID 58278 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].[NH2:20][C:21]1[N:29]=[C:28]2[C:24]([NH:25][CH:26]=[N:27]2)=[C:23](Br)[N:22]=1.C(N(CC)C(C)C)(C)C>C(O)C>[NH2:20][C:21]1[N:29]=[C:28]2[C:24]([N:25]=[CH:26][NH:27]2)=[C:23]([NH:1][CH:2]([C:4]2[N:5]=[C:6]3[S:19][CH:18]=[CH:17][N:7]3[C:8](=[O:16])[C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:3])[N:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 61011392-Amino-6-bromopurineHCID 581114357-(1-aminoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 178463609HCID 178463609, 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), 2-amino-6-bromopurine (0.035 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 C19H17N8OS (M+H)+: m/z=405.1. Found: 405.1. 1H NMR (DMSO-d6, 400 MHz) δ 80.1 (1H, d, J=4.8 Hz), 7.65 (1H, s), 7.55 (1H, d, J=4.8 Hz), 7.47 (2H, m), 7.40 (3H, m), 6.79 (1H, br s), 5.48 (2H, br s), 5.13 (1H, m), 1.29 (3H, d, J=6.8 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-4cdc4365f90d41a18688bafbe3ccdf5d
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

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