Diisopropylethylamine → (R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamide

HRID 2427982Notes

Reaction equation

HRID 2427982 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[N:19]=[C:18]([C:20](OCC)=[O:21])[C:17]([N+:25]([O-])=O)=[C:16]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[N:15]=2)[CH2:9]1)=O)(C)(C)C.ClC1N=C([C:44](OCC)=[O:45])C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.C([N:68]1CCC(N)C1)(OC(C)(C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:36][O:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[N:28]1[C:44](=[O:45])[NH:25][C:17]2[C:16]1=[N:15][C:14]([NH:13][C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)=[N:19][C:18]=2[C:20]([NH2:68])=[O:21]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 86627704(R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate

Product 1

HCID 24937106(R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitro-pyrimidine-4-carboxylate (See Example 30.A) (0.300 g, 0.852 mmol), (R) 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 (0.403 g, 94%). MS (ESI) m/z 503 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-72df888ece614d7b887c6e882dcd30ec
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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