Sodium Carbonate → 3-(2-Chloro-5-(2-thienyl)pyrimidine-4-ylamino)propanol

HRID 1169734ノート

反応式

HRID 1169734 の反応式
[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]=1

参加物

6

反応物 4

HCID 10340Sodium Carbonate2 回HCID 521585Tris(furan-2-yl)phosphaneHCID 27339602-Thiopheneboronic acidHCID 595508483-(2-Chloro-5-iodopyrimidine-4-ylamino)propan-1-ol

生成物 1

HCID 589856463-(2-Chloro-5-(2-thienyl)pyrimidine-4-ylamino)propanol

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  1. addition(7.1 ml, 7.1 mmol) are added (the previously light yellow reaction mixture
  2. customis passed in for 15 mins
  3. distillationDimethoxyethane is distilled off on the rotary evaporator
  4. additionthe residue treated with 250 ml ethyl acetate and 30 ml H2O
  5. stirringstirred vigorously for 30 mins
  6. filtrationthe undissolved substance filtered off at the pump on a G4 frit
  7. washwashed with H2O and ethyl acetate

出典と根拠

ORDレコード
ord-6cbfa82787ca4bb193e27087cc1e8176
出典データセット
uspto-grants-2010_11
特許番号
US07825128B2

反応ノート

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