HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl isothiocyanatoformate → Ethyl (7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-yl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl isothiocyanatoformate | HCID 85320 | — |
| Reactant | 4,6-Dichloro-2-methylpyrimidin-5-amine | HCID 736674 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Ethyl (7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-yl)carbamate | HCID 57476594 | 70.5% |
Reaction Steps
To a mixture of 4,6-dichloro-2-methylpyrimidin-5-amine (1 g, 5.62 mmol) and O-ethyl carbonisothiocyanatidate (0.66 mL, 5.62 mmol) was added toluene (2 mL) to wet the solids completely. The mixture was placed on 100° C. oil bath for 1.5 hours, at which time, the mixture had seized to give a solid mass. The solids were cooled to ambient temperature and triturated with ether, then the resulting solids were collected by filtration to give ethyl 7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-ylcarbamate (1.08 g, 3.96 mmol, 70.5% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.70 (br. s., 1H) 4.30 (q, J=7.19 Hz, 2H) 2.69 (s, 3H) 1.30 (t, J=7.15 Hz, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309577B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-acbc6c8363a3429796dd2c3c9334728c |
| Source note | uspto-grants-2012_11 |