Water → Methyl 2-(2-(4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-ylamino)ethylamino)propanoate

HRID 2267336Notes

Reaction equation

HRID 2267336 reaction equation
Br[CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([C:18]2[S:19][C:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:21][CH:22]=2)[CH:15]=[CH:14][N:13]=1.C(N(CC)C(C)C)(C)C.O>CN1CCCC1>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[C:20]1[S:19][C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][CH2:10][CH2:9][NH:8][CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[N:17]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 95576Methyl 2-bromopropionateHCID 60204267N-(2-aminoethyl)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-amine

Product 1

HCID 60204447Methyl 2-(2-(4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-ylamino)ethylamino)propanoate

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

Methyl 2-bromopropanoate (182 mg, 1.09 mmol) was added to a mixture of N-(2-amino-ethyl)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-amine (300 mg, 0.99 mmol) and N,N-diisopropylethylamine (153 mg, 1.19 mmol) in 1-methylpyrrolidine (8 mL) at rt. After stirring at rt for 24 h, water (50 mL) was added and the mixture extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers were washed with brine (3×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8fc22913d5b42709dc8fb98f9ca8127
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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