Diisopropylethylamine → Cc-90001

HRID 2280765Notes

Reaction equation

[C:1]([NH:5][C:6]1[N:11]=[C:10](S(C)=O)[C:9]([C:15]([NH2:17])=[O:16])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:19][C@H:20]1[CH2:25][C@@H:24]([OH:26])[C@H:23]([CH3:27])[CH2:22][CH2:21]1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[C:1]([NH:5][C:6]1[N:11]=[C:10]([NH:19][C@@H:20]2[CH2:21][CH2:22][C@@H:23]([CH3:27])[C@H:24]([OH:26])[CH2:25]2)[C:9]([C:15]([NH2:17])=[O:16])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirring suspension of 2-(tert-butylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide (0.092 g, 0.359 mmol) and (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride (0.065 g, 0.395 mmol) in DMF (2 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.157 mL, 0.897 mmol) and the reaction was heated to 90° C. overnight. The crude reaction mixture was concentrated under reduced pressure and then ice-cold water (20 mL) was added to the residue. The resulting mixture was vigorously stirred for 1 h and then the product was filtered, washed with water and dried under vacuum to afford 2-(tert-butylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)pyrimidine-5-carboxamide (0.074 g, 0.230 mmol, 64.1% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.94 (br. s., 1H), 8.34 (s, 1H), 6.69 (br. s., 1H), 4.59 (d, J=5.47 Hz, 1H), 3.87 (br. s., 1H), 2.92-3.01 (m, 1H), 2.14 (d, J=10.15 Hz, 1H), 1.91 (d, J=11.71 Hz, 1H), 1.67 (dd, J=13.28, 3.12 Hz, 1H), 1.07-1.24 (m, 3H), 0.91-0.99 (m, 4H). MS (ESI) m/z 322.3 [M+1]+.

Workup

customThe crude reaction mixture
concentrationwas concentrated under reduced pressure
additionice-cold water (20 mL) was added to the residue
filtrationthe product was filtered
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-8c6c1db244a243bfbf736ab3b888c47d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139534B2

Reaction notes

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