Triethylamine → HCID 67238013, compound

HRID 515978Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)[N:3]=1.[NH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]1[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].CCN(CC)CC>CC(N(C)C)=O>[C:29]([O:28][C:27]([NH:26][C@H:21]1[CH2:22][CH2:23][CH2:24][CH2:25][C@H:20]1[NH:19][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)[N:3]=1)=[O:33])([CH3:32])([CH3:30])[CH3:31]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of methyl 2-chloro-4-methyl-6-(1-methyl-1H-pyrazol-4-yl)pyrimidine-5-carboxylate (0.227 g, 0.851 mmol) and tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (0.182 g, 0.851 mmol) in DMA (3 mL) was added Et3N (0.356 mL, 2.55 mmol). The reaction mixture was heated at 90° C. for 4 h. The reaction mixture was cooled to RT and poured onto ice. The solid was filtered and dried under high vacuum to yield the title compound as an off-white foam (170 mg). [M+H] calc'd for C22H32N6O4, 445; found, 445.

Workup

temperatureThe reaction mixture was cooled to RT
additionpoured onto ice
filtrationThe solid was filtered
customdried under high vacuum

Sources & evidence

ORD record: ord-6ee999b90a50479490f47ea4cc184860
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108970B2

Reaction notes

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