Sodium Carbonate → HCID 86699647, compound

HRID 929531Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][C:10]1([CH3:22])[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH2:19][CH2:20][NH2:21])[C:13]=2[O:12][CH2:11]1.C([O-])([O-])=O.[Na+].[Na+]>CC(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:21][CH2:20][CH2:19][C:18]2[C:13]3[O:12][CH2:11][C:10]([CH3:22])([CH3:9])[C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

As shown in step 3-vi of Scheme 3, a solution of 4,6-dichloropyrimidine (111.6 mg, 0.726 mmol), 2-(3,3-dimethyl-2H-benzofuran-7-yl)ethanamine (139 mg, 0.726 mmol), Na2CO3 (231.1 mg, 2.180 mmol) in i-PrOH (5.56 mL) was sealed in a microwave-type tube and heated at 90° C. in an oil bath for 18 hours. The reaction mixture was filtered through a pad of diatomaceous earth, the volatiles removed under reduced pressure, and the residue purified by medium pressure chromatography on silica gel (0 to 100% EtOAc in hexanes) to give 6-chloro-N-(2-(3,3-dimethyl-2,3-dihydrobenzofuran-7-yl)ethyl)pyrimidin-4-amine (Compound 2006) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 1H), 6.94 (d, J=7.3 Hz, 1H), 6.88 (d, J=7.4 Hz, 1H), 6.78 (t, J=7.4 Hz, 1H), 6.25 (s, 1H), 4.20 (d, J=5.9 Hz, 2H), 4.05 (d, J=7.1 Hz, H), 3.47 (s, 2H), 2.83 (t, J=6.6 Hz, 2H), 1.50 (s, 2H) and 1.27 (s, 6H) ppm; ESMS (M+H)=304.06.

Workup

filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
customthe volatiles removed under reduced pressure
customthe residue purified by medium pressure chromatography on silica gel (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-87f00d7c258d4472a01a4ffa98f11e3e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296701B2

Reaction notes

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