Hydrochloric Acid → HCID 18327471, compound

HRID 1004042Notes

Reaction equation

HRID 1004042 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:26][C:27]2[N:32]=[C:31]([S:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=3)[CH:30]=[CH:29][N:28]=2)[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][CH2:22]O.C1(C)C=CC(S([Cl:51])(=O)=O)=CC=1.[ClH:53].[N:54]1[CH:59]=[CH:58][CH:57]=[CH:56]C=1>O>[ClH:51].[ClH:53].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:26][C:27]2[N:32]=[C:31]([S:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=3)[CH:30]=[CH:29][N:28]=2)[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][CH2:22][N:54]1[CH2:56][CH2:57][CH2:58][CH2:59]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 85570p-ToluenesulfonateHCID 18327490HCID 18327490, compound

Product 1

HCID 18327471HCID 18327471, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The tosylate used as starting material was prepared by treating a solution of N-[3,5-dimethoxy-4-(2-hydroxyethoxy)phenyl]-4-(3-methoxyphenylsulphanyl)-2-pyrimidineamine (2.0 g, 4.3 mmol) in pyridine (6 ml) with p-toluenesulphonyl chloride (3.28 g, 17.2 mmol) at room temperature for 2 h. Water (25 ml) was added to the reaction followed by acidification with 2M hydrochloric acid, and this was extracted with ethyl acetate (100 ml). The organic phase was washed with 2M hydrochloric acid (100 ml) and saturated aqueous Na2CO3 (100 ml), dried (MgSO4) and concentrated under reduced pressure to give the desired product as a light brown oil (2.31 g). δH (CDCl3) 8.04 (1H, d, J 5.4 Hz), 7.80 (2H, d, J 8.3 Hz), 7.39-7.30 (3H, s), 7.20-7.13 (2H, m), 7.03-6.99 (2H, m), 6.86 (2H, s), 6.22 (1H, d, J 5.4 Hz), 4.31 (2H, t, J 5.6 Hz), 4.13 (2H, t, J 5.6 Hz), 3.81 (3H, s), 3.77 (6H, s) and 2.43 (3H, s).

Workup

  1. customwas prepared
  2. extractionthis was extracted with ethyl acetate (100 ml)
  3. washThe organic phase was washed with 2M hydrochloric acid (100 ml) and saturated aqueous Na2CO3 (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6baeedfb47584c0eb07b13670c1809c6
Source dataset
uspto-grants-2000_04
Patent number
US06048866

Reaction notes

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