p-Toluenesulfonic acid → HCID 58421637, compound

HRID 406068Notes

Reaction equation

HRID 406068 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.O1[C:16]2([CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[NH:30][C:31]3[C:32]4[C:39]([CH3:40])=[C:38]([C:41]([O:43][CH3:44])=[O:42])[S:37][C:33]=4[N:34]=[CH:35][N:36]=3)[CH2:18][CH2:17]2)[O:15]CC1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[F:29][C:27]1[CH:26]=[CH:25][C:24]([NH:30][C:31]2[C:32]3[C:39]([CH3:40])=[C:38]([C:41]([O:43][CH3:44])=[O:42])[S:37][C:33]=3[N:34]=[CH:35][N:36]=2)=[C:23]([O:22][CH:19]2[CH2:20][CH2:21][C:16](=[O:15])[CH2:17][CH2:18]2)[CH:28]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 58421628HCID 58421628, compound

Product 1

HCID 58421637HCID 58421637, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.000 g p-toluenesulfonic acid was added to 0.500 g methyl 4-(2-(1,4-dioxaspiro[4.5]decan-8-yloxy)-4-fluorophenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (cpd.19.1) in 10 ml THF and 5 ml water. After refluxing overnight the reaction mixture was adjusted to pH 8 using aq. Na2CO3. The aq. layer was extracted with chloroform. The combined extracts were passed through a hydrophobic frit and concentrated to give the desired compound.

Workup

  1. temperatureAfter refluxing overnight the reaction mixture
  2. extractionThe aq. layer was extracted with chloroform
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6f7b6a3fca15451d94c1c1c983ef0cec
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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