HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-(2-Hydroxy-3-(1-(2-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane | HCID 19385012 | — |
| Reactant | 1-(2-Methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine hcl-salt | HCID 131729787 | — |
| Solvent | iPrOH DMSO | HCID 87082799 | — |
| Product | 4-(2-Hydroxy-3-(1-(2-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol | HCID 24936490 | 22% |
Reaction Steps
Synthesis followed SP6 (iPrOH:DMSO 1:1, 1.2 eq. DIEA, 120° C., 48 h), using 200 μmol tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane and 1-(2-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine HCl-salt to give O-silylated intermediate upon purification by prep. HPLC (reversed phase) and prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 6:4:1) with 22% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) and prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 3:7:1.5) with 25% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08207174B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-0fac9fc95e9b4009af2f76ce1059bf82 |
| Source note | uspto-grants-2012_06 |