7-Cyclobutyl-5-(2-phenylquinazolin-7-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine → 3-Cyclobutyl-1-(4-methyl-2-phenyl-quinazolin-7-yl)-imidazo[1,5-a]pyrazin-8-ylamine

HRID 244136Notes

Reaction equation

HRID 244136 reaction equation
C1(N2C3N=CN=C(N)C=3[C:7]([C:15]3[CH:24]=[C:23]4[C:18]([CH:19]=[N:20][C:21]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[N:22]4)=[CH:17][CH:16]=3)=C2)CCC1.Br[C:32]1[N:33]=[C:34]([CH:42]2[CH2:45][CH2:44][CH2:43]2)[N:35]2[CH:40]=[CH:39][N:38]=[C:37]([NH2:41])[C:36]=12>>[CH:42]1([C:34]2[N:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH2:41])[C:36]3=[C:32]([C:15]3[CH:7]=[C:19]4[C:18]([C:17]([CH3:16])=[N:22][C:21]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)=[N:20]4)=[CH:23][CH:24]=3)[N:33]=2)[CH2:45][CH2:44][CH2:43]1

Participants

3

Reactant 2

HCID 536290487-Cyclobutyl-5-(2-phenylquinazolin-7-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 576809341-Bromo-3-cyclobutylimidazo[1,5-a]pyrazin-8-amine

Product 1

HCID 115242883-Cyclobutyl-1-(4-methyl-2-phenyl-quinazolin-7-yl)-imidazo[1,5-a]pyrazin-8-ylamine

Procedure

Synthesized as 7-cyclobutyl-5-(2-phenylquinazolin-7-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine from of 1-bromo-3-cyclobutylimidazo[1,5-a]pyrazin-8-amine (16 mg, 0.06 mmol). Crude material was purified by preparative TLC (silica gel, 5% MeOH in DCM) followed by a recrystallization (EtOAc) and trituration (hexanes) to afford the title compound as a light yellow solid; MS (ES+): m/z 407.1 (100); HPLC: tR (min) 2.44 (OpenLynx, polar—5 min).

Workup

  1. customCrude material was purified by preparative TLC (silica gel, 5% MeOH in DCM)
  2. customfollowed by a recrystallization (EtOAc) and trituration (hexanes)

Sources & evidence

ORD record
ord-111846e36f7e499f85e60aac81897a5f
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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