Ethanethiol → HCID 21882929, compound

HRID 722101Notes

Reaction equation

Br[C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[C:14]=1[Br:25].[CH3:26][CH2:27][SH:28].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Br:25][C:14]1[C:15]([O:23][CH3:24])=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=1[CH2:12][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][C:9]([NH2:11])=[N:10][C:2]=2[S:28][CH2:27][CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-bromo-9-(2-bromo-3,4,5-trimethoxy-benzyl)-9H-purin-2-ylamine (see previous example), EtSH, K2CO3 and THF was placed in a pressure vessel and heated to 70° C. for 6 h. Work-up and purification by preparative TLC (EtOAc:hexane 1:1) gave the title compound. HPLC Rt: 6.039 min. 1H-NMR (CDCl3): δ 7.72 (s, 1H), 6.62 (s, 1H), 5.30 (s, 2H), 4.98 (s, 2H), 3.91 (s, 3H), 3.88 (s, 3H), 3.74 (s, 3H), 3.35–3.29 (q, 2H), 1.44–1.41 (t, 3H).

Workup

customwas placed in a pressure vessel
custompurification by preparative TLC (EtOAc:hexane 1:1)

Sources & evidence

ORD record: ord-0583bd96c71047edbe462cd8331288c6
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138401B2

Reaction notes

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