Potassium Carbonate → (S)-2-(4'-(cyclopropylmethyl)-2-(pyridin-4-ylamino)-4,5'-bipyrimidin-2'-ylamino)propan-1-ol

HRID 1397156Notes

Reaction equation

[CH:1]1([CH2:4][C:5](=O)/[C:6](/[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:12]=2)=[CH:7]\N(C)C)[CH2:3][CH2:2]1.[OH:25][CH2:26][C@@H:27]([NH:29][C:30]([NH2:32])=[NH:31])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]1([CH2:4][C:5]2[C:6]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[N:12]=3)=[CH:7][N:32]=[C:30]([NH:29][C@@H:27]([CH3:28])[CH2:26][OH:25])[N:31]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (Z)-1-cyclopropyl-4-(dimethylamino)-3-(2-(pyridin-4-ylamino)pyrimidin-4-yl)but-3-en-2-one (9) (50 mg, 0.155 mmol) in DMF (541 μl), (S)-1-(1-hydroxypropan-2-yl)guanidine (147 mg, 0.773 mmol) and potassium carbonate (214 mg, 1.546 mmol) were added, and the reaction mixture was stirred at 90° C. for 3 hours. The crude product was purified by reverse-phase HPLC [30-90% organic phase over 15 minutes] followed by Biotage™ silica gel chromatography [10 g SNAP column, 100% DCM to 12% MeOH/DCM] to obtain the desired product (23.9 mg, 41%).

Workup

customThe crude product was purified by reverse-phase HPLC [30-90% organic phase over 15 minutes]

Sources & evidence

ORD record: ord-550d124666ab422082ee8ce47dcabe2f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901147B2

Reaction notes

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