Dimethylformamide → HCID 178489573, compound

HRID 391645Notes

Reaction equation

HRID 391645 reaction equation
[OH:1][C@H:2]1CC[C@H](NC2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)CC1.Cl[C:33]1[N:38]=[C:37]([C:39]([O:41]CC)=O)[C:36]([N+:44]([O-])=O)=[C:35]([NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[O:54][CH3:55])[N:34]=1.[NH2:56][C@H:57]1[CH2:62][CH2:61][C@H:60]([OH:63])[CH2:59][CH2:58]1.C([N:67](C(C)C)CC)(C)C.C[N:74](C)[CH:75]=[O:76]>>[C:75](=[O:76])([O:63][C@H:60]1[CH2:61][CH2:62][C@H:57]([NH:56][C:33]2[N:34]=[C:35]3[C:36]([NH:44][C:2](=[O:1])[N:47]3[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[O:54][CH3:55])=[C:37]([C:39](=[O:41])[NH2:67])[N:38]=2)[CH2:58][CH2:59]1)[NH2:74]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 178470296HCID 178470296, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178489573HCID 178489573, compoundYield 82%

Procedure

Ethyl 2-(trans-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), trans-4-aminocyclohexanol (0.117 g, 1.022 mmol) and diisopropylethylamine 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 (0.303 g, 82%). MS (ESI) m/z 432.5 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-ded6f95d08dc4a5ca0c250c902273e91
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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