Sodium Carbonate → 3-(2-Chloro-5-(2-thienyl)pyrimidine-4-ylamino)propanol
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])[C:5](I)=[CH:4][N:3]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])[C:5]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)=[CH:4][N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
In accordance with procedure 3, 3-(2-chloro-5-iodopyrimidine-4-ylamino)propan-1-ol (1.38 g, 4.4 mmol) and 2-thiophenboronic acid (0.62 g, 4.87 mmol) are dissolved in 15 ml dimethoxyethane under argon, and tri(2-furyl)phosphine (104 mg, 0.45 mmol) and 1 molar Na2CO3 soln. (7.1 ml, 7.1 mmol) are added (the previously light yellow reaction mixture becomes almost colourless and turbid after the Na2CO3 addition). Argon is passed in for 15 mins. Tetrakis(triphenyl-phosphine)palladium (511 mg, 0.44 mmol) is then added and the reaction mixture is stirred for 18 hrs at 75° C. under argon (suspension). Dimethoxyethane is distilled off on the rotary evaporator, the residue treated with 250 ml ethyl acetate and 30 ml H2O, stirred vigorously for 30 mins, and the undissolved substance filtered off at the pump on a G4 frit, and washed with H2O and ethyl acetate: 372 mg residue.
Workup
- addition(7.1 ml, 7.1 mmol) are added (the previously light yellow reaction mixture
- customis passed in for 15 mins
- distillationDimethoxyethane is distilled off on the rotary evaporator
- additionthe residue treated with 250 ml ethyl acetate and 30 ml H2O
- stirringstirred vigorously for 30 mins
- filtrationthe undissolved substance filtered off at the pump on a G4 frit
- washwashed with H2O and ethyl acetate
Sources & evidence
- ORD record
- ord-6cbfa82787ca4bb193e27087cc1e8176
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825128B2
Reaction notes
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