Ethylene Glycol → 4-Methyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(p-tolyl)-4-pyrimidinyl]-amide

HRID 10256

Reaction equation

HRID 10256 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5]C.C(O)CO.[Na].ClC1[N:18]=[CH:17][N:16]=[C:15]([NH:19][S:20](=[O:30])(=[O:29])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[C:14]=1[C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1>CN(C=O)C>[OH:5][CH2:4][CH2:3][O:2][C:1]1[N:18]=[CH:17][N:16]=[C:15]([NH:19][S:20](=[O:29])(=[O:30])[NH:21][C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[C:14]=1[C:31]1[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 80711,2-DimethoxyethaneHCID 5360545Sodium2×HCID 219795524-Methyl-phenyl sulfamic acid-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-amide

Product 1

HCID 219795764-Methyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(p-tolyl)-4-pyrimidinyl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1,2-dimethoxyethan (15 ml) and ethyleneglycol (40 ml) was added sodium (298 mg) in small portions. The mixture was stirred until the sodium was completely dissolved. Then DMF (15 ml), followed by 4-methyl-phenyl sulfamic acid-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-amide (1.0 g, Referential Example 14) was added. Stirring was continued for 4 days at 100° C. The mixture was evaporated and water (150 ml) was added to the residue followed by addition of acetic acid (1.0 ml). The precipitate was filtered off, washed with water and dried. The crude material was purified by chromatography over silicagel with EtOAc/methanol/aquous ammonia (25%)=4/1/0.5 to give 4-methyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(p-tolyl)-4-pyrimidinyl]-amide (500 mg). tR=4.38 (LC); [M+H]+=415.19 (ES+).

Workup

  1. dissolutionwas completely dissolved
  2. additionwas added
  3. customThe mixture was evaporated
  4. additionwater (150 ml) was added to the residue
  5. additionfollowed by addition of acetic acid (1.0 ml)
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customThe crude material was purified by chromatography over silicagel with EtOAc/methanol/aquous ammonia (25%)=4/1/0.5

Sources & evidence

ORD record
ord-542f35727f4d4e29a5f0506e1410f87a
Source dataset
uspto-grants-2006_08
Patent number
US07094781B2

Linked notes

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