Bicarbonate Ion → HCID 68768162, compound

HRID 1272489Notes

Reaction equation

Br.Br[CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15].[NH2:16][CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(=O)(O)[O-]>CN(C)C(=O)C>[NH2:14][C:9]1[N:8]=[C:7]([NH2:15])[C:6]2[C:11](=[N:12][CH:13]=[C:4]([CH2:3][C:17]([CH2:3][C:4]3[N:5]=[C:6]4[C:11](=[N:12][CH:13]=3)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]4[NH2:15])([NH2:16])[C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[N:5]=2)[N:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (51 mg, 0.2 mmol) in anhydrous N,N dimethylacetamide was added 1-aminomethyl-naphthalene (31.67 ul, 0.22 mmol). The reaction mixture was stirred at 50° C. overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 9 mg product was obtained. Yield: 15%; 1H NMR(500 MHz, DMSO-d6): δ 4.0970 (s, 4H), 4.2526 (s, 2H), 7.3530–7.3692 (dd, J1=7.25 Hz, J2=7.25 Hz, 2H), 7.439–7.5202 (m, 2H), 7.5414–7.5553 (d, J=6.94 Hz, 1H), 7.67408–7.69065 (d, J=8.285 Hz, 1H), 7.78789–7.7713 (d, J=8.285 Hz, 1H), 8.14819–8.1313 (d, J=8.44 Hz, 1H), 8.7144 (s, 2H), 8.93305 (s, 2H), 9.23424(s, 2H); ESI-MS: m/z 506 (M++1)

Workup

customThe resulted precipitate was collected
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-9cc5aed14ae045be86e8c0461eec7353
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208493B2

Reaction notes

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