Chloride → 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxylic acid, 4-[5-[(2-methyl-1-oxo-2-propen-1-yl)amino]-3-pyridinyl]-, ethyl ester

HRID 882122Notes

Reaction equation

HRID 882122 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[N:6][CH:7]=1.CCN([CH:28]([CH3:30])[CH3:29])C(C)C.[Cl-].[CH3:32][OH:33]>C(Cl)Cl>[CH3:29][C:28](=[CH2:30])[C:32]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[N:6][CH:7]=1)=[O:33]

Participants

6

Reactant 4

HCID 312ChlorideHCID 887MethanolHCID 81531DiisopropylethylamineHCID 117703138HCID 117703138, compound

Product 1

HCID 715996007H-Pyrrolo[2,3-d]pyrimidine-5-carboxylic acid, 4-[5-[(2-methyl-1-oxo-2-propen-1-yl)amino]-3-pyridinyl]-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl 4-(5-aminopyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (59 mg, 0.14 mmol) in DCM (1.0 mL) was added Hunig's base (0.060 mL, 0.34 mmol) at 0° C. Methacyloyl chloride (0.015 mL, 0.15 mmol) was then added dropwise and the reaction was allowed to warm to room temperature. After being stirred for 17 hours at room temperature, MeOH was added to quench the reaction and the solution was concentrated in vacuo. The crude reaction was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The products were collected and lyophilized to afford a colorless solid. LRMS (ESI) calc'd for C18H18N5O3 [M+H]+: 352, found 352. 1H NMR (600 MHz, DMSO-D6) δ 13.17 (s, 1H), 10.22 (s, 1H), 9.04 (s, 1H), 9.02 (d, 1H, J=1.7 Hz), 8.55 (s, 1H), 8.50 (m, 1H), 8.45 (m, 1H), 5.93 (s, 1H), 5.65 (s, 1H), 3.99 (q, 2H, J=7.2 Hz), 2.01 (s, 3H), 1.00 (t, 3H, J=7.2 Hz).

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationthe solution was concentrated in vacuo
  4. customThe crude reaction
  5. customwas purified by reverse phase HPLC
  6. customThe products were collected
  7. customto afford a colorless solid

Sources & evidence

ORD record
ord-94cdc354ac3c4845a592aeae83ec1f16
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

Loading…