Potassium Carbonate → HCID 178433182, compound

HRID 1371100Notes

Reaction equation

HRID 1371100 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.[NH2:18][C@H:19]([CH2:24][OH:25])[CH2:20][CH:21]([CH3:23])[CH3:22].C([O-])([O-])=O.[K+].[K+]>O>[CH3:22][CH:21]([CH3:23])[CH2:20][C@H:19]([NH:18][C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2[C:3]=1[N:11]=[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]=2)[CH2:24][OH:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111307L-LeucinolHCID 178432852HCID 178432852, compound

Product 1

HCID 178433182HCID 178433182, compoundYield 56.4%

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)) (100 mg, 0.41 mmol), (S)-(+)-leucinol (Aldrich Chemical Company) (0.26 mL, 2.05 mmol) and K2CO3 (0.567 g, 4.1 mmol) in H2O (2.5 mL) to give 75 mg (56%) of the title compound as shiny off-white crystals. Mp: 267-269° C. (dec.). 1H NMR (DMSO-d6; 400 MHz): δ 0.91-0.95 (m, 6), 1.48-1.52 (m, 2), 1.66-1.70 (m, 1), 2.37 (s, 3), 3.50 (br s, 2), 4.39 (br s, 1), 4.90 (br s, 1), 6.65 (d, 1, J=8.4), 6.72 (s, 1), 7.36-7.52 (m, 3), 7.79 (d, 2, J=7.9), 11.35 (br s, 1). MS m/z: 325 (M+1), 323 (M−1). Anal. Calcd for C19H2N4NO: C, 70.34; H, 7.46; N, 17.27. Found: C, 70.14; H, 7.35; N, 17.13.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-aa60f7d1d0c84cad891059dedd480256
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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