2-Thiopheneboronic acid → (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol

HRID 1169726Notes

Reaction equation

HRID 1169726 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:5](I)=[CH:4][N:3]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O>>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:5]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 59550865(R)-2-(2-chloro-5-iodopyrimidine-4-ylamino)propan-1-ol

Product 1

HCID 58985641(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-olYield 70%

Procedure

In the reaction of (R)-2-(2-chloro-5-iodopyrimidine-4-ylamino)propan-1-ol (400 mg, 1.3 mmol) with thiophen-2-boronic acid (e. g.: Aldrich, Acros, Apin) (179 mg, 1.4 mmol) according to procedure 3, the desired product is obtained in 70% yield (240 mg) after chromatographic purification (silica gel, ethyl acetate/hexane (0%-100% ethyl acetate)).

Sources & evidence

ORD record
ord-990d30a3533343598545a0887fb74569
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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