Diisopropylethylamine → HCID 178431857, compound

HRID 1429830Notes

Reaction equation

[NH2:1][CH:2]([C:4]1[N:5]=[C:6]2[S:20][CH:19]=[C:18]([CH3:21])[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:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][NH:27]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[C:18]([CH3:21])=[CH:19][S:20][C:6]3=[N:5][C:4]=2[CH:2]([NH:1][C:23]2[N:31]=[CH:30][N:29]=[C:28]3[C:24]=2[N:25]=[CH:26][NH:27]3)[CH3:3])[CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of single enantiomer 7-(1-aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.125 g, 0.412 mmol) made from above, 6-bromo-9H-purine (0.148 g, 0.742 mmol), and N,N-diisopropylethylamine (0.144 mL, 0.824 mmol) in ethanol (1.5 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 (0.076 g, 44%). LCMS calculated for C20H17FN7OS (M+H)+: m/z=422.1. Found: 422.0. 1H NMR (DMSO-d6, 500 MHz) δ 8.05 (2H, s), 7.43 (1H, m), 7.24˜7.14 (5H, m), 6.99 (1H, s), 5.08 (1H, m), 2.59 (3H, s), 1.29 (3H, d, J=6.5 Hz) ppm. 19F NMR (DMSO-d6, 376.3 MHz) δ −114 ppm.

Workup

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

Sources & evidence

ORD record: ord-c7da0c244dca47838a48bbb5ca433cc2
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940752B2

Reaction notes

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