Diisopropylethylamine → Acetic acid 3-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenyl ester

HRID 1066503

Reaction equation

HRID 1066503 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)(=[O:17])=[O:16])[C:11]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[C:10]([O:34][CH3:35])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N([CH:42]([CH3:44])C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1([O:61][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(O)(=O)C>[CH3:35][O:34][C:10]1[C:11]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[C:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)(=[O:17])=[O:16])[N:13]=[C:8]([C:4]2[CH:3]=[C:2]([O:1][C:42](=[O:61])[CH3:44])[CH:7]=[CH:6][CH:5]=2)[N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 98485845-Methyl-pyridine-2-sulfonic acid [2-(3-hydroxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

Product 1

HCID 54541401Acetic acid 3-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

49.5 mg of 5-methyl-pyridine-2-sulfonic acid [2-(3-hydroxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide, product of example 1, dissolved in acetontrile (3 ml) was treated at RT subsequently with 25.8 mg of n-ethyldiisopropylamine, 53 mg of benzotriazol-1-yloxytris-(dimethylamino)-phosphonium hexafluorophosphate and, 0.5 h later, with 72 mg of acetic acid. The mixture was stirred for 12 h, partitioned between water and EtOAc. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with Me2Cl2/EtOAc: 8/1). Combination of the purified fractions and evacuation in vacuo afforded acetic acid 3-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenyl ester as a white solid. ISP mass spectrum, m/e 537.2 (M+1 calculated for C26H24N4O7S: 537).

Workup

  1. custompartitioned between water and EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe residue was purified on a silica gel chromatography column (eluted with Me2Cl2/EtOAc: 8/1)

Sources & evidence

ORD record
ord-f78707999338421ab286f05cc6a4e10d
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Linked notes

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