alpha-Bromo-o-chlorotoluene → HCID 11573144, compound

HRID 550714Notes

Reaction equation

C([O:4][N:5]1[C:10](=[O:11])[C:9]2[S:12][CH:13]=[CH:14][C:8]=2[N:7]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18](Br)[CH:17]=2)[C:6]1=[O:23])C=C.BrCC1C=CC=CC=1[Cl:32]>>[Cl:32][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][N:7]1[C:8]2[CH:14]=[CH:13][S:12][C:9]=2[C:10](=[O:11])[N:5]([OH:4])[C:6]1=[O:23]

Participants

Reactant 2

HCID 11905alpha-Bromo-o-chlorotoluene

HCID 67200730HCID 67200730, compound

Product 1

HCID 11573144HCID 11573144, compound

Procedure

3-Allyloxy-1-(3-bromo-benzyl)-1H-thieno[3,2-d]pyrimidine-2,4-dione (from previous example) was alkylated with 1-bromomethyl-2-chloro-benzene via general procedure B2. The crude intermediate was deprotected via general procedure D2. The final product was purified by mass triggered preparative HPLC. 1H NMR (DMSO-d6) δ 10.65 (bs, 1H), 8.10 (d, 1H, J=5.1 Hz), 7.52 (dd, 1H, J=1.5, 7.8 Hz), 7.32 (dt, 1H, J=1.5, 7.5 Hz), 7.25 (dt, 1H, J=1.5, 7.5 Hz), 7.13 (d, 1H, J=5.4 Hz), 6.96 (dd, 1H, J=1.5, 7.5 Hz), 5.31 (s, 2H); Electrospray MS: 309 (M+H); retention time: 2.31 min.

Workup

customThe final product was purified by mass

Sources & evidence

ORD record: ord-72cfe4b522434bec84c85f098af5fbf0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947691B2

Reaction notes

Loading…