Diisopropylethylamine → HCID 178463610, compound

HRID 58275Notes

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].[NH2:21][C:22]1[N:30]=[C:29]2[C:25]([NH:26][CH:27]=[N:28]2)=[C:24](Br)[N:23]=1.C(N(CC)C(C)C)(C)C>C(O)C>[NH2:21][C:22]1[N:30]=[C:29]2[C:25]([N:26]=[CH:27][NH:28]2)=[C:24]([NH:1][CH:2]([C:4]2[N:5]=[C:6]3[S:20][CH:19]=[CH:18][N:7]3[C:8](=[O:17])[C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH3:3])[N:23]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 7-(1-amino ethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.025 g, 0.086 mmol), 2-amino-6-bromopurine (0.033 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 C19H16FN8OS (M+H)+: m/z=423.1. Found: 423.0. 1H NMR (DMSO-d6, 400 MHz) δ 7.98 (1H, d, J=4.8 Hz), 7.63 (1H, s), 7.52 (1H, d, J=4.8 Hz), 7.46 (1H, m), 7.20 (2H, m), 6.84 (1H, br s), 5.41 (1H, br s), 5.07 (1H, m), 1.26 (3H, d, J=6.8 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-6c6b8cc8d9d147b3a9bd1c3af4ed40b6
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434746B2

Reaction notes

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