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

HRID 570493Notes

Reaction equation

HRID 570493 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][S: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[S: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 89652Methyl 3-amino-2-thiophenecarboxylateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 669578463-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl esterYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6386tert-ButanolSolvent

Procedure

A suspension of 6-chloro-7-deazapurine (750 mg; 4.88 mmol), methyl 3-amino-2-thiophenecarboxylate (1.15 g; 7.33 mmol) and concentrated hydrochloric acid (410 μL; 4.9 mmol) in tert-butanol (15 mL) was microwaved at 75° C. for 3 h. The reaction mixture was diluted with methanol (15 mL) and filtered. The aqua solid was washed with methanol and dried under vacuo to afford the hydrochloric salt of 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester (900 mg, 59%) as a green-gray solid (HPLC: 99%, RT: 6.50 min). 1H NMR (DMSO-d6) 12.47 (br s, 1H), 10.68 (br s, 1H), 8.44 (s, 1H), 8.08 (br s, 1H), 8.02 (d, J=5.5 Hz, 1H), 7.47 (dd, J=3.3, 2.2 Hz, 1H), 6.66 (br s, 1H), 3.83 (s, 3H); MS (m/z) 275 [M+H]+.

Workup

  1. customwas microwaved at 75° C. for 3 h
  2. filtrationfiltered
  3. washThe aqua solid was washed with methanol
  4. customdried under vacuo

Sources & evidence

ORD record
ord-a93593927dbe45aea904fddbcc78f410
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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