Diisopropylethylamine → HCID 24937107, compound

HRID 391650Notes

Reaction equation

HRID 391650 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-5b2b36c6f9e94dff97128859d97d8a33
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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