Chloride → HCID 67983538, compound

HRID 1397174Notes

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]=[CH:4][N:3]=1.[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.CS(C)=O.[Cl-]>C1COCC1>[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=3)[CH:5]=[CH:4][N:3]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2-chloro-4,5′-bipyrimidin-2′-amine (30) (110 mg, 0.530 mmol) in THF (5298 μl), 4-Fluoroaniline (100 μl, 1.060 mmol) was added. DMSO (1 mL) was added to dissolve the starting chloride, and the suspension was heated to 150° C. in the microwave for 2 hours. The crude reaction mixture was filtered through a syringe filter, then purified by reverse-phase HPLC [30-100% organic phase over 15 minutes] to obtain a reddish purple product. The product was triturated with acetone and acetonitrile, then filtered to obtain a slightly gray solid as the desired product (19 mg, 13% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.15 (t, J=9.09 Hz, 2 H) 7.22 (s, 2 H) 7.31 (d, J=5.05 Hz, 1 H) 7.79 (dd, J=9.09, 5.05 Hz, 2 H) 8.44 (d, J=5.05 Hz, 1 H) 8.99 (s, 2 H) 9.59 (s, 1H). HRMS (ES+) for C14H11FN6.H+ [MH+]: calcd, 283.1107. found, 283.1108. UV-LC: 100/100% UV purity at 214/254 nm; tR=1.07 minutes over 7.75 minutes.

Workup

additionwas added
customThe crude reaction mixture
filtrationwas filtered through a syringe
filtrationfilter
custompurified by reverse-phase HPLC [30-100% organic phase over 15 minutes]
customto obtain a reddish purple product
customThe product was triturated with acetone and acetonitrile
filtrationfiltered

Sources & evidence

ORD record: ord-9c64119e60924cee85c6907c7ad478c1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901147B2

Reaction notes

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