Diisopropylethylamine → HCID 66647786, compound

HRID 2427999Notes

Reaction equation

HRID 2427999 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 86627715HCID 86627715, compound

Product 1

HCID 66647786HCID 66647786, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-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), (R) 1-boc-(aminomethyl)pyrrolidine (0.207 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 (0.430 g, 97%). MS (ESI) m/z 517.5 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-6ffde68272eb420fbf86befc45ca4de5
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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