Dimethylamine → HCID 18768058, compound

HRID 480011Notes

Reaction equation

[CH3:1][NH:2][CH3:3].[NH:4]([C:11]1[C:16]([Br:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:30])[CH2:27][CH2:28]Cl)=[CH:21][CH:20]=2)[N:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O1CCCC1.CN(C=O)C.C(Cl)Cl>[NH:4]([C:11]1[C:16]([Br:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:30])[CH2:27][CH2:28][N:2]([CH3:3])[CH3:1])=[CH:21][CH:20]=2)[N:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of dimethylamine in tetrahydrofuran (2.0M; 4 ml) was added to a solution of 4-anilino-5-bromo-2-[4-(3-chloropropionamido)anilino]pyrimidine (Method 37; 60 mg, 0.135 mmol) in DMF (0.2 ml). The solution was heated at 80° C. for 1 hour, diluted with DCM (4 ml) and loaded onto a Varian Mega Bond Elut column. Elution with 0-10% 2.0M methanolic ammonia solution in DCM gave the product (5.4 mg, 9%). MS (MH+): 455, 457; HPLC (RT): 2.70.

Workup

washElution with 0-10% 2.0M methanolic ammonia solution in DCM

Sources & evidence

ORD record: ord-364e4acbe6af462a8d5c3c77159df2be
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649608B2

Reaction notes

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