Morpholine → HCID 86665768, compound

HRID 2092561Notes

Reaction equation

HRID 2092561 reaction equation
[Br:1][C:2]1[CH:11]=[N:10][C:9]2[C:8](Cl)=[N:7][C:6]([Cl:13])=[N:5][C:4]=2[CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[N:10][C:9]2[C:8]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:7][C:6]([Cl:13])=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 72207571HCID 72207571, compound

Product 1

HCID 86665768HCID 86665768, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of crude 7-bromo-2,4-dichloro-pyrido[3,2-d]pyrimidine (2.85 g, 0.0102 mol) in DCM (25 mL) at 0° C. was added morpholine (1.8 g, 0.0204 mol). The reaction was continued at 0° C. for 30 min. The volatiles were evaporated and subjected to column chromatography (60-120 silica gel, 0-12% ethyl acetate in hexane) to get the title compound as a light yellow solid [0.35 g, 26%]. 1H NMR (300 MHz, DMSO-d6): δ 8.68 (d, J=2.7 Hz, 1H), 8.19 (d, J=2.4 Hz, 1H), 3.86-3.89 (m, 8H); LC-MS (ESI): Calculated mass: 328.0; Observed mass: 330.8 [M+H]+ (RT: 1.50 min).

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-46d9de8dd779417e875cbd281530ff6c
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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