Pyrrolidine → N4-(4-chlorophenyl)6-pyrrolidin-1-yl-pyrimidine-4,5-diamine

HRID 1246802

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[NH2:16].[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>C([O-])(O)=O.[Na+]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:4]2[C:3]([NH2:16])=[C:2]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[N:7]=[CH:6][N:5]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Chloro-N4-(4-chlorophenyl)-pyrimidine-4,5-diamine I-(1A-1)a (114 mg, 0.45 mmol) and pyrrolidine (1 ml, excess) were combined and heated with stirring at 100° C. for 2 hours. The reaction mixture was diluted with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, and evaporated to dryness to yield the desired compound I-(17A-1)a (131 mg, quantitative) as an orange-brown solid: +ESI MS (M+1) 290.3; 1H NMR (500 MHz, CD3OD) δ 7.85 (s, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.8 Hz, 2H), 3.63 (m, 4H), 1.96 (m, 4H).

Workup

temperatureheated
extractionextracted with ethyl acetate
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-71d7bad0cd694211a11f6ce4945b6b59
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129239B2

Linked notes

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