1-Iodopropane → 4-(5-Methyl-2-propylsulfanyl-pyrimidin-4-yl)-4H-pyrrole-2-carboxylic acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide

HRID 852307Notes

Reaction equation

HRID 852307 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([SH:25])[N:19]=2)[CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:26](I)[CH2:27][CH3:28]>N>[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[N:14]=[CH:15][CH:16]([C:18]2[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([S:25][CH2:26][CH2:27][CH3:28])[N:19]=2)[CH:17]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 336431-IodopropaneHCID 178430803HCID 178430803, compound

Product 1

HCID 865950124-(5-Methyl-2-propylsulfanyl-pyrimidin-4-yl)-4H-pyrrole-2-carboxylic acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a solution of 4-(2-mercapto-5-methyl-pyrimidin-4-yl)-1H-pyrrole-2-carboxylic acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide (7.7 mmol, 2.74 mmol) in aqueous ammonia (15%) was added at room temperature n-propyliodide (11.6 mmol, 1.1 mL). The solution was stirred overnight at room temperature. The resulting solid was collected by filtration and used directly for the next step. 1H NMR consistent with the structure.

Workup

  1. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-1a51d0135d6343b282d9a5228c41c997
Source dataset
uspto-grants-2007_08
Patent number
US07253187B2

Reaction notes

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