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

HRID 391647Notes

Reaction equation

HRID 391647 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-4df211e8443940cf8430fe2660fbe6f9
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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