HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 86632017, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Reactant | HCID 86632018 | HCID 86632018 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 86632017 | HCID 86632017 | 79.7% |
Reaction Steps
Charge 4-chloro-5-iodo-7H-pyrrolo[2,3-]pyrimidine (5.0 g, 1.0 eq), 2-methyl-3-butyn-2-ol (9.02 g, 6.0 eq), TEA (1.68 g, 0.93 eq), CuI (1.36 g, 0.4 eq), DMF (62.5 mL) and THF (187.5 mL) at RT under argon atmosphere. Stir the reaction mass at RT under argon atmosphere for 5 min. Charge Pd(PPh3)4 (1.03 g, 0.05 eq) and stir the reaction mass at 45° C. for 16 h. Monitor the reaction by TLC (65% CHCl3: 23% Hexane: 12% Acetone). Concentrate the reaction mass under vacuum. Charge ethyl acetate and give washing with water and saturated aq. sodium chloride. Dry the organic layer over anhydrous Na2SO4 and concentrate it under vacuum. Crystallize the compound in 65% CHCl3: 23% hexane: 12% Acetone to give the desired compound (3.35 g, 79.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08093383B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-2f0578a46c2d4839a6aaa699e1e5ac0e |
| Source note | uspto-grants-2012_01 |