HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-(2-Hydroxy-3-(1-(thieno[3,2-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-(Thieno[3,2-d]pyrimidin-4-yl)piperidin-4-amine hcl-salt | HCID 131729788 | — |
| Solvent | iPrOH DMSO | HCID 87082799 | — |
| Product | 4-(2-Hydroxy-3-(1-(thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol | HCID 24937016 | 13% |
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-(thieno[3,2-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 13% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) with 37% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08207174B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-be90e808a8f6403d8e22cf63c06a0b38 |
| Source note | uspto-grants-2012_06 |