4-Toluenesulfonyl chloride → HCID 59441641, compound

HRID 1014548Notes

Reaction equation

HRID 1014548 reaction equation
[Cl:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[C:10]([F:11])[C:5]2=[C:4]([Cl:12])[N:3]=1.CCN(C(C)C)C(C)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+].C(Cl)Cl>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([F:11])=[CH:9][N:8]([S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 23716255Sodium bicarbonate methylene chlorideHCID 178505976HCID 178505976, compound

Product 1

HCID 59441641HCID 59441641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,4-dichloro-5-fluoro-1H-pyrrolo[2,3-d]pyrimidine (1.65 g, 8.01 mmol, crude material from abovefl) in dichloromethane (100 ml) was treated with DIPEA (2.80 ml, 16.02 mmol) and p-toluenesulfonylchoride (1.756 g, 9.21 mmol) and stirred for 24 hours. The mixture was poured into saturated sodium bicarbonate/DCM and the organic layer was dried over sodium sulfate, filtered, stripped onto celite, and purified by column chromatography (10% EtOAc/Hex). The chromatographic residue (still containing multiple impurities) was further purified with a 65% isocratic MeCN mobile phase on a Luna C18 5 um, 21×150mm column, 20 mL/min, UV @275 nm. The final purity of 2,4-dichloro-5-fluoro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine was estimated at 99.5% at 254 nm using the same method (1.128 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.23 (d, J=2.20 Hz, 1H), 7.96 (d, J=8.24 Hz, 2H), 7.47 (d, J=8.79 Hz, 2H), 2.34 (s, 3H).

Workup

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. custompurified by column chromatography (10% EtOAc/Hex)
  4. additionThe chromatographic residue (still containing multiple impurities)
  5. customwas further purified with a 65% isocratic MeCN mobile phase on a Luna C18 5 um, 21×150mm column, 20 mL/min, UV @275 nm

Sources & evidence

ORD record
ord-4a43ec9504fb4513af421dcf8139e362
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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