Water → 2-[3-(2-Isopropylpyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

HRID 1796116Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([OH:13])([CH3:12])[CH3:11])=[N:6][C:5]=12.Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[N:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:21]([C:17]1[N:18]=[C:19]([C:3]2[N:4]3[CH:9]=[CH:8][C:7]([C:10]([OH:13])([CH3:11])[CH3:12])=[N:6][C:5]3=[N:1][CH:2]=2)[CH:20]=[CH:15][N:16]=1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(imidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (Example 21, Step 3) (339 mg, 1.9 mmol), 4-chloro-2-isopropylpyrimidine (300 mg, 1.9 mmol), Cs2CO3 (1.25 g, 3.8 mmol) and tetrakis(triphenylphosphine)-palladium(0) (221 mg, 10 mol %) in 1,4-dioxane (10 ml) was heated at 100° C. under N2 for 18 h. Water (75 ml) was added and the organic products were extracted with CH2Cl2 (3×50 ml). The combined organic layers were concentrated under reduced pressure and then purified by column chromatography on silica, using 10% EtOH/EtOAc as eluent, to yield 2-[3-(2-isopropylpyrimidin-4-yl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol (121 mg, 22%): 1H NMR (400 MHz, d6-DMSO) δ 10.21 (1H, d, J 8.1), 8.76 (1H, s), 8.72 (1H, d, J 6.1), 7.88 (1H, d, J 6.1), 7.66 (1H, d, J 8.1), 5.57 (1H, s), 3.24 (1H, septet, J 7.7), 1.53 (6H, s), 1.37 (6H, d, J 7.7); m/z (ES+) 298 (M+H+).

Workup

extractionthe organic products were extracted with CH2Cl2 (3×50 ml)
concentrationThe combined organic layers were concentrated under reduced pressure
custompurified by column chromatography on silica

Sources & evidence

ORD record: ord-fb02a3a611824e118311cf284bd7894a
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030128B2

Reaction notes

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