HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphate → Di-tert-butyl ((4-(3,4-dichlorophenyl)-2-((2-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetyl)imino)thiazol-3(2H)-yl)methyl) phosphate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphate | HCID 1061 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N-[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetamide | HCID 5136098 | — |
| Reactant | Di-Tert-Butyl Iodomethyl Phosphate | HCID 58196853 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Di-tert-butyl ((4-(3,4-dichlorophenyl)-2-((2-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetyl)imino)thiazol-3(2H)-yl)methyl) phosphate | HCID 86666698 | — |
Reaction Steps
The title compound was prepared according to the general procedure as described in method A for the preparation of phosphate derivatives by coupling N-[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetamide (150 mg, 0.322 mmol) with freshly prepared di-tert-butyl iodomethyl phosphate (Intermediate 2) (395.16 mg, 1.129 mmol) in the presence of sodium hydride (60% dispersion in mineral oil, 20 mg, 0.483 mmol) in dry DMF (2 ml) with to yield 135 mg of pure product as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 1.48 (br s, 18H), 3.35 (s, 3H), 3.47 (s, 2H), 3.62 (s, 3H), 5.71 (s, 2H), 6.36 (br s, 2H), 7.42-7.50 (m, 1H), 7.60-7.72 (m, 1H), 8.02 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08592398B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-7db42e1a86264df5ba9124702dc29fe3 |
| Source note | uspto-grants-2013_11 |