Diisopropylethylamine → HCID 24937107, compound

HRID 2427985Notes

Reaction equation

HRID 2427985 reaction equation
[CH2:1]([O:3]C(C1C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=C(Cl)N=1)=O)C.C(OC([N:32]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38]2[N:43]=[C:42]([C:44](OCC)=[O:45])[C:41]([N+:49]([O-])=O)=[C:40]([NH:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=3[O:59][CH3:60])[N:39]=2)[CH2:33]1)=O)(C)(C)C.C([N:68]1CCC(N)C1)(OC(C)(C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:60][O:59][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=1[N:52]1[C:1](=[O:3])[NH:49][C:41]2[C:40]1=[N:39][C:38]([NH:37][C@H:34]1[CH2:35][CH2:36][NH:32][CH2:33]1)=[N:43][C:42]=2[C:44]([NH2:68])=[O:45]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 86627708HCID 86627708, compound

Product 1

HCID 24937107HCID 24937107, compoundYield 134.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-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), (S) 1-boc-3-aminopyrrolidine (0.190 g, 1.022 mmol) and diisopropylethylamine (0.164 g., 1.27 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 (0.424 g, 99%). MS (ESI) m/z 503 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-f5d7959af0534608a555d33b119cc06a
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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