Dimethylformamide → HCID 136337156, compound

HRID 1428812Notes

Reaction equation

HRID 1428812 reaction equation
Cl[C:2]1[N:11]=[C:10]([O:12]COCCOC)[C:9]2[C:4](=[CH:5][C:6]([Cl:19])=[CH:7][CH:8]=2)[N:3]=1.[NH:20]1[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:22]=[N:21]1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>Cl>[CH2:28]([O:27][C:25]([C:23]1[CH:24]=[N:20][N:21]([C:2]2[NH:11][C:10](=[O:12])[C:9]3[C:4](=[CH:5][C:6]([Cl:19])=[CH:7][CH:8]=3)[N:3]=2)[CH:22]=1)=[O:26])[CH3:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 86644118HCID 86644118, compound

Product 1

HCID 136337156HCID 136337156, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,7-dichloro-4-(2-methoxy-ethoxymethoxy)-quinazoline (0.68 g, 2.2 mmol), ethyl pyrazole-4-carboxylate (0.34 g, 2.4 mmol), Cs2CO3 (1.2 g, 3.6 mmol) and anhydrous DMF (10 mL) was heated to 120° C. for 20 min, and then was cooled to 0° C. The mixture was carefully diluted with 1 M aq. HCl (30 mL). The mixture was allowed to warm to rt and the precipitate was collected by filtration to provide the titled compound (0.35 g, 50%). MS (Cl): mass calcd. for C14H11ClN4O3, 318.7; m/z found, 317.0 [M−H]−. 1H NMR (400 MHz, DMSO-d6): 13.04 (br s, 1H), 8.99 (s, 1H), 8.32 (s, 1H), 8.11 (d, J=8.5 Hz, 1H), 7.75 (s, 1H), 7.54 (dd, J=8.5, 2.1 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturewas cooled to 0° C
  2. temperatureto warm to rt
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4dc43a9d96f74b47ac52b5be4519f25b
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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