HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-chloro-N-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5,7-Dichlorothiazolo(5,4-d)pyrimidine | HCID 609639 | — |
| Reactant | 3-(2-(Methoxymethyl)pyrrolidin-1-yl)aniline | HCID 68379331 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 5-chloro-N-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine | HCID 86671784 | 64.1% |
Reaction Steps
A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (170 mg, 0.83 mmol), 3-(2-(methoxymethyl)pyrrolidin-1-yl)aniline (170 mg, 0.83 mmol) and DIEA (214 g, 1.66 mmol) in 15 mL of DMSO was stirred at room temperature overnight. 100 mL of water were added, the mixture was extracted with ethyl acetate (3×30 mL). The organic layer was washed with water (2×30 mL) and brine (30 mL), concentrated under reduced pressure to give 5-chloro-N-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 64%) as a yellow solid. LC-MS: 376 [M+H]+, tR=1.75 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08921383B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-1a91775b80fe4d359ae99ac26c5b7e9b |
| Source note | uspto-grants-2014_12 |