Hydrochloric Acid → HCID 44612039, compound

HRID 1842592Notes

Reaction equation

HRID 1842592 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][NH:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.C[C:13]1[C:21]2[C:20](N)=[N:19][CH:18]=N[C:16]=2[O:15][CH:14]=1.Cl.[CH:24](O)(C)[CH3:25]>>[CH3:16][O:15][C:14]1[CH:13]=[CH:21][C:20]([N:19]([CH3:18])[C:2]2[C:3]3[CH:11]=[CH:10][NH:9][C:4]=3[N:5]=[C:6]([CH3:8])[N:7]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 109208984-CHLORO-2-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINEHCID 552840015-Methylfuro[2,3-D]pyrimidin-4-amine

Product 1

HCID 44612039HCID 44612039, compoundYield 80%

Procedure

Compound 4 (0.005 mol, 0.835 g) was added to a solution of 4-methoxy-N-methylaniline (5, 0.006 mol, 0.822 g) in i-propanol (10 ml) with drops of conc. HCl. The resulting solution was transferred to a microwave vial (20 ml) and irradiated at 110° C. After 6 h, the reaction was completed and AAG20 was obtained after the chromatographic purification as a white solid (1.01 g) with 80% yield. TLC Rf=0.85 (CH3OH:CHCl3=1:5). 1H NMR (DMSO-d6): δ 2.65 (s, 3H, 2-CH3), 3.62 (s, 3H, N—CH3), 3.84 (s, 3H, OCH3), 6.99 (bs, 4H, C6H4), 7.11-7.13 (d, 1H, 5-H), 7.39-7.41 (d, 1H, 6-H), 12.44 (s, 1H, 7-H, D2O exchanged). Anal. Calcd. (C15H16N4O. 0.3688 CHCl3.), C, 59.10; H, 5.28; N, 17.94; Found C, 58.98; H, 5.65; N, 18.16.

Workup

  1. customirradiated at 110° C
  2. customAAG20 was obtained
  3. customafter the chromatographic purification as a white solid (1.01 g) with 80% yield

Sources & evidence

ORD record
ord-f60127244a5b4008bd5f65b4c03b661c
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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