HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine → (S)-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-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine | HCID 51003674 | — |
| 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 | (S)-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 57713819 | — |
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) (263 mg) with AD-mix-α (Aldrich, 1.41 g) in t-BuOH:water 1:1: (7 mL) at rt for 3 days, followed by quench (NaHSO3, 1.6 g), work-up, and preparative HPLC gave the title compound (69 mg), as a solid. HPLC Rt=4.36 min
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07544672B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-9e13779cf5cf43ec8a06622edb5d63c1 |
| Source note | uspto-grants-2009_06 |