Potassium Carbonate → HCID 86696512, compound

HRID 1615915Notes

Reaction equation

CC1(C)C(C)(C)OB([CH:9]2[CH2:11][CH:10]2[CH2:12][NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O1.Cl[C:26]1[N:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.[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>[F:32][C:29]1[CH:28]=[N:27][C:26]([CH:9]2[CH2:11][CH:10]2[CH2:12][NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:31][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of benzyl ((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)methyl)carbamate (500 mg, 1.510 mmol), 2-chloro-5-fluoropyrimidine (45 mg, 0.340 mmol), potassium carbonate (100 mg, 0.724 mmol), and tetrakis(triphenylphosphine) palladium (0) (10 mg, 8.65 μmol) in dioxane (2 mL) and water (0.4 mL) was heated to 100° C. in a sealed vial for 16 h. The mixture was diluted with EtOAc and washed with sat'd sodium carbonate. The EtOAc layer was concentrated to an amber oil. The crude product was purified by silica gel chromatography using 0-30% EtOAc/hexane as the eluent to give benzyl ((2-(5-fluoropyrimidin-2-yl)cyclopropyl)methyl)carbamate as a colorless oil (220 mg, 42%). 1H NMR (400 MHz, CHLOROFORM-d) d 8.45-8.31 (m, 2H), 7.36-7.30 (m, 5H), 5.10 (s, 2H), 4.07 (br. s., 1H, NH), 3.39-3.15 (m, 2H), 2.19 (dt, J=8.5, 4.4 Hz, 1H), 1.78-1.62 (m, 1H), 1.31 (dt, J=8.7, 4.5 Hz, 1H), 1.09-0.95 (m, 1H). LCMS: M+1=302.2.

Workup

washwashed with sat'd sodium carbonate
concentrationThe EtOAc layer was concentrated to an amber oil
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-444beee48a834cfe932e2902d3d9b604
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765767B2

Reaction notes

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