HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Bis(dihydroquinidine)phthalazine → (R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,4-Bis(dihydroquinidine)phthalazine | HCID 11217202 | — |
| Reactant | 4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-(3-methylbut-3-en-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine | HCID 57713816 | — |
| Reactant | 2-Methylpropan-2-ol--water (1/1) | HCID 71401949 | — |
| Product | (R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol | HCID 57713869 | — |
Reaction Steps
Treatment of 4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-(3-methylbut-3-en-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (see example 51) (357 mg) with AD-mix-β (Aldrich, 1.57 g) in t-BuOH:water 1:1: (10 mL) at rt for 18 h, followed by quench (NaHSO3, 1.2 g), work-up, and silica gel flash chromatography (1→10% MeOH inDCM) gave the title compound (61 mg) and recovered starting material (263 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07544672B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-37dea16f9f8c4c1ea15cf44305b0a9f3 |
| Source note | uspto-grants-2009_06 |