4-(8-(3-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile → 4-(8-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile

HRID 1042288Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([C:17]4[C:18]([NH:23][C:24]5[C:25]([CH3:43])=[CH:26][CH:27]=[C:28]6[C:33]=5[N:32]=[CH:31][N:30]=[C:29]6[NH:34][C:35]5[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=5)=[N:19][CH:20]=[CH:21][CH:22]=4)=[C:11]3[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[NH:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([C:17]3[C:18]([NH:23][C:24]4[C:25]([CH3:43])=[CH:26][CH:27]=[C:28]5[C:33]=4[N:32]=[CH:31][N:30]=[C:29]5[NH:34][C:35]4[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=4)=[N:19][CH:20]=[CH:21][CH:22]=3)=[C:11]2[CH:10]=[N:9]1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 4-(8-(3-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile (120 mg, 203 μmol) in TFA (3 ml) was heated at 65° C. for 3 hr. TFA was removed under vacuum. MeOH (2N, NH3) (20 ml) was added and then solvent was removed under vacuum. The product was purified by flash chromatography eluting with MeOH/DCM (1-5%) to give 4-(8-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile. MS (ESI pos. ion) m/z 471 (M+H+).

Workup

customTFA was removed under vacuum
additionMeOH (2N, NH3) (20 ml) was added
customsolvent was removed under vacuum
customThe product was purified by flash chromatography
washeluting with MeOH/DCM (1-5%)

Sources & evidence

ORD record: ord-e4f7e095a28a48abaf665cfae76a65c9
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557830B2

Reaction notes

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