Diisopropylethylamine → 4-(tert-Butylamino)-2-(4-hydroxybicyclo[2.2.1]heptan-1-ylamino)-pyrimidine-5-carboxamide

HRID 2280796Notes

Reaction equation

[C:1]([NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8](S(C)(=O)=O)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:20][C:21]12[CH2:27][C:24]([OH:28])([CH2:25][CH2:26]1)[CH2:23][CH2:22]2.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:20][C:21]23[CH2:27][C:24]([OH:28])([CH2:25][CH2:26]2)[CH2:23][CH2:22]3)[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

4-(tert-Butylamino)-2-(methylsulfonyl)pyrimidine-5-carboxamide (0.165 g, 0.606 mmol; synthesis described herein), 4-aminobicyclo[2.2.1]heptan-1-ol hydrochloride (0.105 g, 0.644 mmol) and DIEA (0.337 ml 1.931 mmol) were mixed in DMF (8 mL) and heated at 90° C. overnight. The solvent was evaporated and the residue was purified by silica gel column chromatography (0-10% methanol in ethyl acetate) to give the desired product. (41 mg, 0.127 mmol, 21%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.43 (br. s., 0H) 8.32 (s, 1H) 7.07 (br. s., 1H) 4.88 (br. s., 1H) 1.94-2.14 (m, 2H) 1.61-1.87 (m, 6H) 1.49-1.60 (m, 2H) 1.42 (s, 9H). MS (ESI) m/z 320.0 [M+1]+

Workup

customsynthesis
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (0-10% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-de26183713d04b5eaf1b4e1845518fe7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139534B2

Reaction notes

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