Diisopropylethylamine → HCID 66647723, compound

HRID 2428003Notes

Reaction equation

HRID 2428003 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]1[N:20]=[C:19]([C:21](OCC)=[O:22])[C:18]([N+:26]([O-])=O)=[C:17]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH3:37])[N:16]=1)=O)(C)(C)C.ClC1N=C([C:45](OCC)=[O:46])C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.C([N:69]1CCCC1CN)(OC(C)(C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:37][O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N:29]1[C:45](=[O:46])[NH:26][C:18]2[C:17]1=[N:16][C:15]([NH:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)=[N:20][C:19]=2[C:21]([NH2:69])=[O:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2756484(+-)-2-(Aminomethyl)-1-N-Boc-pyrrolidineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 86627719HCID 86627719, compound

Product 1

HCID 66647723HCID 66647723, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-Ethyl 2-((1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methylamino)-6-(2-methoxy-phenylamino)-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-(aminomethyl)pyrrolidine (0.206 g, 1.02 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 (0.416 g, 95%). MS (ESI) m/z 517.3 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-15605303b5c74138ab8a0426eea1494c
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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