Potassium Carbonate → HCID 178433141, compound

HRID 1371115Notes

Reaction equation

HRID 1371115 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[CH2:18]([NH2:24])[CH:19]1[O:23][CH2:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:8][C:6]1[NH:5][C:4]2[C:3]([N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=2)=[C:2]([NH:24][CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][O:23]2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 253298TetrahydrofurfurylamineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433141HCID 178433141, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared according to the method described in Example 26 by employing 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (0.10 g, 0.41 mmol), tetrahydrofurfuryl amine (Aldrich Chemical Company) (0.212 mL, 2.05 mmol) and K2CO3 (0.34 g, 2.50 mmol) in H2O (2.5 mL) to obtain crude pink solids. Recrystallization from EtOH/MeOH gave 0.044 g (35%) of the title compound as an off-white solid. Mp: 280° C. 1H NMR (CDCl3; 500 MHz): δ 1.59 (m, 1), 1.87 (m, 2), 2.00 (m, 1), 2.39 (s, 3), 3.48 (m, 1), 3.71 (m, 2), 3.86 (t, 1, J=7.3), 4.06 (m, 1), 6.74 (s, 1), 6.95 (s, 1), 7.38 (t, 1, J=7.1), 7.51 (t, 2, J=7.6), 7.80 (d, 2, J=8.0), 11.41 (s, 1). MS m/z: 309 (M+1). Anal. Calcd for C18H20N4O: C, 70.11; H, 6.54; N, 18.17. Found: C, 69.88; H, 6.51; N, 18.03.

Workup

  1. customThis compound was prepared
  2. customto obtain crude pink solids
  3. customRecrystallization from EtOH/MeOH

Sources & evidence

ORD record
ord-c17b17204db34793a61e9b2df312d8fd
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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