1,2-Dichloroethane → HCID 25256061, compound

HRID 886820Notes

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-cb092cbabeed40b498f78ea50ddb620c
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247410B2

Reaction notes

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