Dimethylformamide → HCID 86632017, compound

HRID 419736Notes

Reaction equation

HRID 419736 reaction equation
[Cl:1][C:2]1[C:7]2N(I)[CH2:9][CH2:10][C:6]=2[N:5]=[CH:4][N:3]=1.[CH3:12][C:13]([OH:17])(C#C)[CH3:14].C[N:19]([CH:21]=O)[CH3:20].C1COCC1>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)=O.CCCCCC.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]2[C:6]([C:10]#[C:9][C:13]([CH3:14])([OH:17])[CH3:12])=[CH:21][NH:19][C:20]=2[N:5]=[CH:4][N:3]=1

Participants

10

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 82582-Methyl-3-butyn-2-olHCID 86632018HCID 86632018, compound

Product 1

HCID 86632017HCID 86632017, compoundYield 79.7%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 180AcetoneSolventHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

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%).

Workup

  1. concentrationConcentrate the reaction mass under vacuum
  2. customCharge ethyl acetate and give
  3. washwashing with water and saturated aq. sodium chloride
  4. dry with materialDry the organic layer over anhydrous Na2SO4
  5. concentrationconcentrate it under vacuum
  6. customCrystallize the compound in 65% CHCl3

Sources & evidence

ORD record
ord-2f0578a46c2d4839a6aaa699e1e5ac0e
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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