Potassium Carbonate → HCID 71582503, compound

HRID 2172615Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:28])[N:4]([C:17]2[CH:22]=[C:21]([C:23](=O)[C:24]#[CH:25])[CH:20]=[CH:19][C:18]=2[CH3:27])[C:5]([CH3:16])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[N:11]=[C:12]([CH3:15])[S:13][CH:14]=1.Cl.[OH:30][C:31]([CH3:36])([CH3:35])[C:32]([NH2:34])=[NH:33].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:3](=[O:28])[N:4]([C:17]2[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][N:34]=[C:32]([C:31]([OH:30])([CH3:36])[CH3:35])[N:33]=3)[CH:20]=[CH:19][C:18]=2[CH3:27])[C:5]([CH3:16])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[N:11]=[C:12]([CH3:15])[S:13][CH:14]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 5-bromo-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-6-(2-methyl-thiazol-4-ylmethoxy)-3H-pyrimidin-4-one of Step D (64 mg, 0.14 mmol) in acetonitrile (1 mL) was added 2-hydroxy-2-methylpropionamidine HCl (30 mg, 0.21 mmol) and potassium carbonate (60 mg, 0.42 mmol) and the slurry was heated at 75° C. for two hours and at ambient temperature for eighteen hours. The reaction was filtered to remove excess salts. The filtrate was concentrated and purified via normal phase chromatography (ethyl acetate/heptane) to provide the title compound as a white solid (30 mg, 39% yield). MS (M, M+2): 542, 544; 1H NMR (400 MHz, chloroform-d) δ ppm, 1.64 (s, 6H), 2.16 (s, 3H), 2.21 (s, 3H), 2.76 (s, 3H), 5.59-5.67 (m, 2H), 7.26 (s, 1H), 7.54-7.58 (m, 2H), 7.92 (s, 1H), 8.14 (d, J=8.61, 1H), 8.78 (d, J=5.48, 1H).

Workup

filtrationThe reaction was filtered
customto remove excess salts
concentrationThe filtrate was concentrated
custompurified via normal phase chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record: ord-0cc66951582c4984a244ccf63e31e571
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056110B2

Reaction notes

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