Furan, 2-(bromomethyl)tetrahydro- → HCID 11551918, compound
Reaction equation
COC1C=C(OC)C=CC=1C[O:6][N:7]1[C:12](=[O:13])[C:11]2[S:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:16][C:10]=2[NH:9][C:8]1=[O:23].Br[CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][O:33]1>>[OH:6][N:7]1[C:12](=[O:13])[C:11]2[S:14][C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:16][C:10]=2[N:9]([CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][O:33]2)[C:8]1=[O:23]Participants
3
Procedure
3-(2,4-dimethoxy-benzyloxy)-6-phenyl-1H-thieno[3,2-d]pyrimidine-2,4-dione (from previous example) was alkylated with 2-bromomethyl-tetrahydro-furan via general procedure B1. This crude intermediate was deprotected via general procedure D1 to give the title compound which was purified by mass-triggered preparative HPLC. 1H NMR (DMSO-d6) δ 7.80 (d, 2H, J=8.1 Hz), 7.78 (s, 1H), 7.52-7.44 (m, 3H), 4.23-4.06 (m, 3H), 3.74 (dd, 1H, J=7.8, 13.8 Hz), 3.59 (dd, 1H, J=7.5, 13.8 Hz), 2.05-1.58 (m, 4H); Electrospray MS: 345 (M+H); retention time: 2.43 min.
Sources & evidence
- ORD record
- ord-ed3e129a2fd64995ac9b7d3804d14da6
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947691B2
Reaction notes
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