Hydrochloric Acid → HCID 178489614, compound

HRID 1066518Notes

Reaction equation

HRID 1066518 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([C:11]2[N:16]=[C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=3)(=[O:20])=[O:19])[C:14]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])=[C:13]([O:37][CH3:38])[N:12]=2)[CH:8]=[CH:7][N:6]=1)C=C.[BH4-].[Na+].Cl>C1COCC1>[OH:4][C:5]1[CH:10]=[C:9]([C:11]2[N:16]=[C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=3)(=[O:20])=[O:19])[C:14]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])=[C:13]([O:37][CH3:38])[N:12]=2)[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54194846HCID 54194846, compound

Product 1

HCID 178489614HCID 178489614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 mg of 5-methyl-pyridine-2-sulfonic acid [2-(2-allyloxy-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide, product of example 39, were suspended in THF (5 ml), treated at RT with 2.2 mg of tetrakis-(triphenylphosphine)palladium and stirred for 5 minutes after which time 6.4 mg of NaBH4 were added. The mixture was stirred for 2 h until the reaction was completed according to TLC analysis. The reaction mixture was poured into cold diluted HCl, the product extracted into AcOEt. The organic layer was dried over NaSO4 and the solvent removed in vacuo to give 5-methyl-pyridine-2-sulfonic acid [2-(2-hydroxy-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as a light yellow solid. ISN mass spectrum, m/e 494.1 (M−1 calculated for C23H21N5O6S: 494).

Workup

  1. additionwere added
  2. extractionthe product extracted into AcOEt
  3. dry with materialThe organic layer was dried over NaSO4
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ce3a518b14f648ffa9f370a2b080024b
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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