Triethylamine → 4-{2-[(6-{[4-(Dimethylphosphoryl)phenyl]amino}pyrimidin-4-yl)-amino]ethyl}benzene sulfonamide

HRID 921373Notes

Reaction equation

HRID 921373 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([P:15]([CH3:18])([CH3:17])=[O:16])=[CH:11][CH:10]=2)[CH:3]=1.C(N(CC)CC)C.[NH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>C(O)C>[CH3:17][P:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([S:35]([NH2:38])(=[O:36])=[O:37])=[CH:33][CH:34]=3)[CH:3]=2)=[CH:10][CH:11]=1)([CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 866688076-chloro-N-[4-(dimethylphosphoryl)phenyl]pyrimidin-4-amine

Product 1

HCID 670532844-{2-[(6-{[4-(Dimethylphosphoryl)phenyl]amino}pyrimidin-4-yl)-amino]ethyl}benzene sulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-chloro-N-[4-(dimethylphosphoryl)phenyl]pyrimidin-4-amine (prepared as in Example 59: 0.12 mmol) in 2 mL of ethanol is added 50 L of triethylamine and 4-(2-aminoethyl)benzene-sulfonamide (23 mg, 0.12 mmol). The mixture can be microwaved at 120 degrees until formation of the desired compound. The reaction mixture can be filtered through a syringe filter and purified by prep-HPLC.

Sources & evidence

ORD record
ord-995ec9b45f724b059ff579f6861fbe4a
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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