Ethanolamine → 4-(2-(2-Fluoropropoxy)pyridin-3-ylamino)-N-(2-hydroxyethyl)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxamide

HRID 532294Notes

Reaction equation

HRID 532294 reaction equation
[F:1][CH:2]([CH3:25])[CH2:3][O:4][C:5]1[C:10]([NH:11][C:12]2[C:13]3[C:20]([CH3:21])=[C:19]([C:22]([OH:24])=O)[S:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:9][CH:8]=[CH:7][N:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:59]([CH2:61][NH2:62])[OH:60]>CN(C=O)C>[F:1][CH:2]([CH3:25])[CH2:3][O:4][C:5]1[C:10]([NH:11][C:12]2[C:13]3[C:20]([CH3:21])=[C:19]([C:22]([NH:62][CH2:61][CH2:59][OH:60])=[O:24])[S:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584132524-(2-(2-Fluoropropoxy)pyridin-3-ylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

Product 1

HCID 584133434-(2-(2-Fluoropropoxy)pyridin-3-ylamino)-N-(2-hydroxyethyl)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-(2-Fluoropropoxy)pyridin-3-ylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylic acid (36.2 mg), HATU (42 mg) and Hünig's base (34 μl) were dissolved in DMF (2 ml) and ethanolamine (9 μl) was added. The reaction was stirred at room temperature for 2 h. The reaction mixture was purified directly by chromatography.

Workup

  1. customThe reaction mixture was purified directly by chromatography

Sources & evidence

ORD record
ord-043f359bc85545e1a2250c57c9a0205d
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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