Potassium Carbonate → HCID 178433076, compound

HRID 1371101Notes

Reaction equation

HRID 1371101 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.[NH:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[CH2:23][OH:24].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]([N:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[CH2:23][OH:24])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 640091L-ProlinolHCID 178432852HCID 178432852, compound

Product 1

HCID 178433076HCID 178433076, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared according to the method described in Example 2 by employing 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (70 mg, 0.287 mmol), (S)-(+)-2-pyrrolidinemethanol (Aldrich Chemical Company) (0.14 mL, 1.44 mmol) and K2CO3 (0.397 g, 2.87 mmol) in H2O (2 mL) to give 61.9 mg (70%) of the title compound as an off-white solid. An analytical sample was obtained by recrystallization from EtOH. Mp: 255-256° C. 1H NMR (CDCl3; 500 MHz): δ 2.06-2.14 (m, 4), 2.54 (s, 3), 3.76 (d, 1, J=9.23), 3.84 (dd, 1, J=2.0, 11.1), 3.96-3.98 (m, 1), 4.11 (q, 1, J=7.6, 7.9), 4.55-4.57 (m, 1), 6.68 (s, 1), 7.35-7.45 (m, 3), 7.61 (d, 2, J=7.4), 9.17 (br s, 1). MS m/z: 167 (base), 307 (M−1). Anal. Calcd for C18H20N4O: C, 70.11; H, 6.54; N, 18.17. Found: C, 70.00; H, 6.59; N, 18.11.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b829afc64ea24c04ad09d3c30f5dcfbd
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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