Dimethylamine → HCID 58980920, compound

HRID 1181828Notes

Reaction equation

[NH:1]([C:3]1[N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5](=[O:15])[CH:4]=1)[NH2:2].[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH:26]=O.[C:28]([C:31]1[CH:32]=[C:33]([CH:37]=O)[N:34]([CH3:36])[CH:35]=1)(=[O:30])[CH3:29].C(C1C=[C:44](C2N(CC3C4C(=CC=C(Cl)C=4)NC=3)N=C3C=2C(=O)N(C)C(=O)N3CC(C)C)[N:45](C)[CH:46]=1)(=O)C.I(Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.CNC>C1COCC1.CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][N:2]1[C:37]([C:33]2[N:34]([CH3:36])[CH:35]=[C:31]([C:28](=[O:30])[CH2:29][N:45]([CH3:46])[CH3:44])[CH:32]=2)=[C:4]2[C:3]([N:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2=[O:15])=[N:1]1

Participants

Conditions

Temperature: 65 °C

Procedure

This compound was made in three steps following the procedure described above, starting with 6-hydrazino-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione, and condensing first 5-chloro-1H-indole-3-carbaldehyde, followed by 4-acetyl-1-methyl-1H-pyrrole-2-carbaldehyde. To the isolated 3-(4-acetyl-1-methyl-1H-pyrrol-2-yl)-2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione in anhydrous THF was added benzyltrimethylammonium dichloroiodate and heated at 65° C. for 1 h. The isolated chloromethyl derivative was treated with dimethylamine in N,N-dimethylformamide for 0.5 h. The crude reaction product was purified by semi-prep RPHPLC eluting with water/acetonitrile/trifluoroacetic acid mixtures. 550.3 (M+H).

Workup

customThe crude reaction product
customwas purified by semi-prep RPHPLC
washeluting with water/acetonitrile/trifluoroacetic acid mixtures

Sources & evidence

ORD record: ord-e9c0bfb5d5274348bd932980396e5d76
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285558B2

Reaction notes

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