Water → HCID 53710627, compound

HRID 1066519Notes

Reaction equation

HRID 1066519 reaction equation
[Na].CO[C:4]([C:6]1[CH:11]=[C:10]([C:12]2[N:17]=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=3)(=[O:21])=[O:20])[C:15]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:14]([O:40][CH3:41])[N:13]=2)[CH:9]=[CH:8][N:7]=1)=[NH:5].[H-].[Na+].O>CN(C=O)C>[C:4]([C:6]1[CH:11]=[C:10]([C:12]2[N:17]=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=3)(=[O:21])=[O:20])[C:15]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:14]([O:40][CH3:41])[N:13]=2)[CH:9]=[CH:8][N:7]=1)#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydride2×HCID 69289426HCID 69289426, compound

Product 1

HCID 53710627HCID 53710627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2.93 g of 4-[4-(5-isopropyl-pyridine-2-sulfonylamino)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carboximidic acid methyl ester sodium salt in DMF (60 ml) was added under ice cooling NaH (0.8 g of a 60% NaH suspension in oil). The mixture was stirred for 1,5 h at 0° C. The mixture was poured into water, the pH adjusted to pH=6 and the product extracted into EtOAc. The organic layer was washed with water, dried over Na2SO4 and the solvent removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with Me2Cl2/EtOAc: 5/1). Combination of the purified fractions and evacuation in vacuo afforded 5-isopropyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as a light yellow crystalline solid. ISN mass spectrum, m/e 531.1 (M−1 calculated for C26H24N6O5S: 531).

Workup

  1. extractionthe product extracted into EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue was purified on a silica gel chromatography column (eluted with Me2Cl2/EtOAc: 5/1)

Sources & evidence

ORD record
ord-1446d666c9f447c5baf9873bad8025ce
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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