Aniline → 6-(4-Tert.butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid phenylamide

HRID 341970Notes

Reaction equation

HRID 341970 reaction equation
CCN(C(C)C)C(C)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32]([C:36]1[CH:41]=[CH:40][C:39]([S:42]([NH:45][C:46]2[N:51]=[C:50]([C:52](O)=[O:53])[N:49]=[C:48]([O:55][CH2:56][CH2:57][OH:58])[C:47]=2[O:59][C:60]2[CH:65]=[CH:64][CH:63]=[C:62]([O:66][CH3:67])[CH:61]=2)(=[O:44])=[O:43])=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>C(#N)C>[C:26]1([NH:25][C:52]([C:50]2[N:49]=[C:48]([O:55][CH2:56][CH2:57][OH:58])[C:47]([O:59][C:60]3[CH:65]=[CH:64][CH:63]=[C:62]([O:66][CH3:67])[CH:61]=3)=[C:46]([NH:45][S:42]([C:39]3[CH:40]=[CH:41][C:36]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:37][CH:38]=3)(=[O:43])=[O:44])[N:51]=2)=[O:53])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 442139556-(4-Tert-butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid

Product 1

HCID 442139576-(4-Tert.butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid phenylamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.2 ml of Hunig base, 0.052 g of bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride and 0.01 ml of aniline were added to a solution of 0.053 g of 6-(4-tert.butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid in 5 ml of acetonitrile. After 3 hours the reaction mixture was evaporated and partitioned between ethyl acetate and water. The organic phase was dried and evaporated, and the residue purified over silica gel with chloroform. There was obtained 0.032 g of 6-(4-tert.butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid phenylamide, m.p. 143° C., MS: (M-H)- 591.

Workup

  1. customAfter 3 hours the reaction mixture was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. customevaporated
  5. customthe residue purified over silica gel with chloroform

Sources & evidence

ORD record
ord-d18c51f8171449879e579fe419077776
Source dataset
uspto-grants-1999_01
Patent number
US05856484

Reaction notes

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