Cesium carbonate → HCID 59198407, compound

HRID 1920833Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH:5]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[NH2:21][C:22]1[CH:23]=[N:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:18]1[CH2:19][CH2:20][N:15]([C:4]2[N:3]=[C:2]([NH:21][C:22]3[CH:23]=[N:24][C:25]4[C:30]([CH:31]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:7]=[C:6]([C:8]3[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=3)[CH:5]=2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-chloro-6-morpholino-4,5′-bipyrimidin-2′-amine (10 mg), 3-amino-quinoline (9.8 mg), Pd(OAc)2 (1.5 mg), BINAP (6.3 mg), and cesium carbonate (15.5 mg) in THF (1 mL) was heated in a microwave at 110° C. for 10 minutes. The crude product was filtered and concentrated under reduced pressure. The product was purified by preparative HPLC to give 6-morpholino-N2-(quinolin-3-yl)-4,5′-bipyrimidine-2,2′-diamine. LCMS (m/z): 401.0 (MH+). Rt=1.83 min.

Workup

filtrationThe crude product was filtered
concentrationconcentrated under reduced pressure
customThe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-e5b8130759df467c830bc065dda8b572
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173647B2

Reaction notes

Loading…