Hydrochloric Acid → 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carboxylic acid methyl ester

HRID 570498Notes

Reaction equation

HRID 570498 reaction equation
[CH:1]1[C:5]2[C:6](Cl)=[N:7][CH:8]=[N:9][C:4]=2[NH:3][CH:2]=1.[NH2:11][C:12]1[CH:16]=[CH:15][O:14][C:13]=1[C:17]([O:19][CH3:20])=[O:18].Cl>C(O)(C)(C)C.CO>[CH3:20][O:19][C:17]([C:13]1[O:14][CH:15]=[CH:16][C:12]=1[NH:11][C:6]1[C:5]2[CH:1]=[CH:2][NH:3][C:4]=2[N:9]=[CH:8][N:7]=1)=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 45790120Methyl 3-aminofuran-2-carboxylate

Product 1

HCID 669577963-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carboxylic acid methyl esterYield 18%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6386tert-ButanolSolvent

Procedure

A suspension of 6-chloro-7-deazapurine (100.00 mg; 0.65 mmol), methyl 3-amino-2-furoate (138 mg; 0.98 mmol) and concentrated hydrochloric acid (55 μL; 0.65 mmol) in tert-butanol (2 mL) was microwaved at 75° C. for 3 h. The reaction mixture was diluted with methanol (2 mL) and purified by chromatography on a SP1 Biotage system, using dichloromethane and methanol as eluents to afford 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-furan-2-carboxylic acid methyl ester (30 mg, 18%) as a white solid. (HPLC: 99%, RT: 5.43 min). 1H NMR (DMSO-d6) 12.03 (br s, 1H), 8.99 (br s, 1H), 8.40 (s, 1H), 7.90 (d, J=2.2 Hz, 1H), 7.71 (d, J=1.8 Hz, 1H), 7.38 (dd, J=3.3, 2.2 Hz, 1H), 6.60 (dd, J=3.3, 1.8 Hz, 1H), 3.90 (s, 3H); MS (m/z) 259 [M+H]+.

Workup

  1. customwas microwaved at 75° C. for 3 h
  2. custompurified by chromatography on a SP1 Biotage system

Sources & evidence

ORD record
ord-2f4dd97f11304b72b7a1a033a6cc5c40
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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