Diisopropylethylamine → HCID 178489570, compound

HRID 391659Notes

Reaction equation

HRID 391659 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:14]=[C:13]([C:15](OCC)=[O:16])[C:12]([N+:20]([O-])=O)=[C:11]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[N:10]=2)[CH2:4][CH2:3]1.ClC1N=C([C:39](OCC)=[O:40])C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.[NH2:56][C@@H]1CC[C@H](O)CC1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:10]=[C:11]3[C:12]([NH:20][C:39](=[O:40])[N:23]3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])=[C:13]([C:15]([NH2:56])=[O:16])[N:14]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 178470295HCID 178470295, compoundHCID 178511714HCID 178511714, compound

Product 1

HCID 178489570HCID 178489570, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(cis-4-hydroxycyclohexylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (See Example 30.A) (0.300 g, 0.852 mmol), cis-4-aminocyclohexanol (0.155 g, 1.022 mmol) and diisopropylethylamine (0.274 g, 2.13 mmol) were reacted according to General Procedure C, except at room temperature and in dimethylformamide (5 mL). The crude reaction mixture was condensed and purified using Biotage chromatography (0-100% ethyl acetate in hexanes) to afford the title compound (0.342 g, 93%). MS (ESI) m/z 432.0 [M+1]+.

Workup

  1. customThe crude reaction mixture
  2. customcondensed
  3. custompurified

Sources & evidence

ORD record
ord-03e55e8d9d244a9380a14e17f2563d63
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

Loading…