Trifluoroacetic acid → 2-(3-Acetamidophenylamino)-4-(pyrrolidin-3-ylmethylamino)pyrimidine-5-carboxylic acid

HRID 384267Notes

Reaction equation

HRID 384267 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][CH2:19][CH:20]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)[C:15]([C:32](=[O:34])N)=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=[O:36]>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][CH2:19][CH:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)[C:15]([C:32]([OH:34])=[O:36])=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58098654Tert-butyl 3-((2-(3-acetamidophenylamino)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 580988022-(3-Acetamidophenylamino)-4-(pyrrolidin-3-ylmethylamino)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-((2-(3-acetamidophenylamino)-5-carbamoylpyrimidin-4-ylamino)methyl)pyrrolidine-1-carboxylate (65 mg, 0.138 mmol) in TFA (1 mL) and CH2Cl2 mL) was stirred at room temperature for 2 h. TFA and CH2Cl2 were removed in vacuo. The residue was purified by HPLC to give the titled compound (25 mg). MS 370.3 (M+H); UV 206.4, 244.2 nm.

Workup

  1. customTFA and CH2Cl2 were removed in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-ddd3e8439bda41deae14a171efca48ef
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

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