Trifluoroacetic acid → HCID 178510739, compound

HRID 1504085Notes

Reaction equation

HRID 1504085 reaction equation
[OH:1][C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:21]([OH:27])([C:23]([F:26])([F:25])[F:24])=[O:22]>ClCCl>[F:24][C:23]([F:26])([F:25])[C:21]([OH:27])=[O:22].[NH2:13][CH2:12][CH2:11][C:9]1[S:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([OH:1])[C:3]=2[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453129HCID 178453129, compound

Product 1

HCID 178510739HCID 178510739, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-(2-[4-hydroxythieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (600 mg, 2.03 mmol, 1.00 equiv) in 25 mL of dichloromethane at 0° C. was added 4 mL of CF3COOH and the resulting solution was stirred for 6 hours at room temperature. The resulting mixture was concentrated under vacuum to give 6-(2-aminoethyl)thieno[2,3-d]pyrimidin-4-ol trifluoroacetate (570 mg, 91%) as a yellow oil which was used directly in the next step without further purification. MS (ES): m/z 196 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-68ab11e9cb9c458cab99ea2321243082
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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