Isopropanol → Methyl 4-[4-cyano-2-(2-fluoro-1-fluoromethyl-ethoxy)phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

HRID 532308Notes

Reaction equation

HRID 532308 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[CH3:15])=[O:4].[NH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=1[O:25][CH:26]([CH2:29][F:30])[CH2:27][F:28].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(C)C>O>[C:21]([C:20]1[CH:23]=[CH:24][C:17]([NH:16][C:12]2[C:7]3[C:6]([CH3:15])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[S:14][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:18]([O:25][CH:26]([CH2:27][F:28])[CH2:29][F:30])[CH:19]=1)#[N:22]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 584133514-Amino-3-(2-fluoro-1-fluoromethyl-ethoxy)-benzonitrile

Product 1

HCID 58413326Methyl 4-[4-cyano-2-(2-fluoro-1-fluoromethyl-ethoxy)phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (0.2 g), 4-amino-3-(2-fluoro-1-fluoromethyl-ethoxy)-benzonitrile (0.17 g), p-toluenesulfonic acid monohydrate (0.16 g) and isopropanol (3.0 ml) were stirred at 90° C. for 2 hours. Then the mixture was poured in water and filtrated. The solid was washed with water and dried in an oven at 70° C.

Workup

  1. filtrationfiltrated
  2. washThe solid was washed with water
  3. customdried in an oven at 70° C.

Sources & evidence

ORD record
ord-4365643e9d8e463da0be4002c7551a6d
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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