1,2-Dichloroethane → HCID 25256061, compound

HRID 1913949Notes

Reaction equation

[N:1]1([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[CH:16]3[CH2:20][CH2:19][NH:18][CH2:17]3)=[C:9]([C:21]3[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:28][C:29]1[S:33][C:32]([C:34](O)=[O:35])=[CH:31][CH:30]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:27][C:24]1[N:23]=[CH:22][C:21]([C:9]2[N:8]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH:16]2[CH2:20][CH2:19][N:18]([C:34]([C:32]3[S:33][C:29]([CH3:28])=[CH:30][CH:31]=3)=[O:35])[CH2:17]2)=[CH:26][N:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-(2-morpholin-4-yl-9-pyrrolidin-3-yl-9H-purin-6-yl)-pyrimidin-2-ylamine (37 mg, 0.08 mmol) in DMF was added 5-methyl-thiophene-2-carboxylic acid (15 mg, 0.104 mmol, 1.3 eq), EDC (20 mg, 0.104 mmol, 1.3 eq), HOBt (14 mg, 0.104 mmol, 1.3 eq) and diisopropylethylamine (32 μL, 0.184 mmol, 2.3 eq). The mixture was stirred at 50° C. for 16 hrs. Then NaHCO3 was added and the mixture extracted twice with ethyl acetate. The combined organic layers were further washed with brine before drying over Na2SO4. The crude product was purified by chromatography to afford the title compound as yellow solid (14.4 mg).

Workup

extractionthe mixture extracted twice with ethyl acetate
washThe combined organic layers were further washed with brine
dry with materialbefore drying over Na2SO4
customThe crude product was purified by chromatography

Sources & evidence

ORD record: ord-71ada215e31444b1aebbe05acc731bd9
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609838B2

Reaction notes

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