[4-(2-tert-Butoxycarbonylaminoethylamino)-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester → [4-(2-Aminoethylamino)-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

HRID 348494Notes

Reaction equation

HRID 348494 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][S:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][CH2:15][NH:16]C(OC(C)(C)C)=O)[C:10]([C:24](=[O:33])[NH:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:9][N:8]=1)[CH3:2]>FC(F)(F)C(O)=O.ClCCl>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][S:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][CH2:15][NH2:16])[C:10]([C:24](=[O:33])[NH:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[CH:9][N:8]=1)[CH3:2]

Participants

3

Reactant 1

HCID 69522205[4-(2-tert-Butoxycarbonylaminoethylamino)-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

Product 1

HCID 69523574[4-(2-Aminoethylamino)-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl esterYield 112.7%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

[4-(2-tert-Butoxycarbonylaminoethylamino)-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester (113 mg, 0.23 mmol) was dissolved in a trifluoroacetic acid/dichloromethane solution (50%, 4 mL) and the resulting solution was stirred under N2 for 2 h. The solvent was removed by rotary evaporation, and trituration with diethyl ether was attempted. The resulting gummy solid was dissolved in water and lyophilized to yield the titled product (102 mg, 88% as trifluoroacetic acid salt) as a hygroscopic and flocculent white solid. 1H NMR: (d6-DMSO) δ 10.28 (s, 1H), 8.64 (m, 1H), 8.60 (s, 1H), 7.65 (in, 2H), 7.18 (t, 2H), 4.09 (q, 2H), 3.98 (s, 2H), 3.62 (m, 2H), 2.98 (m, 2H), 1.17 (t, 3H).

Workup

  1. customThe solvent was removed by rotary evaporation, and trituration with diethyl ether
  2. dissolutionThe resulting gummy solid was dissolved in water

Sources & evidence

ORD record
ord-c20f7d521bec4ab3b9fa8427c17a72a9
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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