Diisopropylethylamine → HCID 24936850, compound

HRID 2427979Notes

Reaction equation

HRID 2427979 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10]CC)=O)[CH:5]([N+:13]([O-])=O)[CH:4]([N:16]([CH2:25][C:26]([O:28]CC)=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[N:3]=1.ClC1N=C(C(OCC)=O)C([N+]([O-])=O)=C(Cl)[N:33]=1.C[O:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1NCC(OCC)=O.C(N(C(C)C)CC)(C)C>>[OH:48][C:49]1[CH:50]=[C:51]([C:2]2[N:7]=[C:6]([C:8]([NH2:33])=[O:10])[C:5]3[NH:13][C:26](=[O:28])[CH2:25][N:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])[C:4]=3[N:3]=2)[CH:52]=[CH:53][CH:54]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2761044Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylateHCID 19711182N-(2-Methoxyphenyl)glycine ethyl esterHCID 57474653HCID 57474653, compound

Product 1

HCID 24936850HCID 24936850, compound

Procedure

Ethyl 2-chloro-6-((2-ethoxy-2-oxoethyl)(2-methoxyphenyl)amino)-5-nitro-5,6-dihydro-pyrimidine-4-carboxylate. Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (3.0 g, 11.27 mmol), ethyl 2-(2-methoxyphenylamino)acetate (2.35 g, 11.27 mmol) and diisopropylethylamine (4.36 g, 33.81 mmol) were reacted according to General Procedure C and partitioned between water and ethyl acetate (3×) to afford the title compound without purification (2.05 g, 41%). MS (ESI) m/z 439.2 [M+1]+, 441.4 [M+2]+.

Workup

  1. custompartitioned between water and ethyl acetate (3×)

Sources & evidence

ORD record
ord-2576927264214bbfb4bda55c4b02aea0
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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