Cesium carbonate → HCID 58413232, compound

HRID 532311Notes

Reaction equation

HRID 532311 reaction equation
[C:1]([O:5][C:6](=[O:10])[CH:7](Br)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[C:20]3[C:27]([CH3:28])=[C:26]([C:29]([O:31][CH3:32])=[O:30])[S:25][C:21]=3[N:22]=[CH:23][N:24]=2)=[C:14]([OH:33])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O>[CH3:32][O:31][C:29]([C:26]1[S:25][C:21]2[N:22]=[CH:23][N:24]=[C:19]([NH:18][C:15]3[CH:16]=[CH:17][C:12]([F:11])=[CH:13][C:14]=3[O:33][CH:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:10])[CH3:8])[C:20]=2[C:27]=1[CH3:28])=[O:30]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 58413076Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate2×

Product 1

HCID 58413232HCID 58413232, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromopropionic acid tert-butyl-ester (1.4 g) was added to methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate (Intermediate III) (2.00 g) and cesium carbonate (4.8 g) in ACN (50 ml) and stirred at 60° C. for 2 hours. The mixture was diluted with water, filtrated and washed with water.

Workup

  1. filtrationfiltrated
  2. washwashed with water

Sources & evidence

ORD record
ord-d7e315cc129044658d0db68a660d6e75
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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