Sodium Carbonate → HCID 66549142, compound

HRID 1410054Notes

Reaction equation

HRID 1410054 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([CH:48]=[CH:49][CH:50]=2)[CH2:33][NH:34][C:35]2[CH:47]=[CH:46][C:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:37][CH:36]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O.O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([NH:11][C:4]2[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=[C:2]([C:30]3[CH:31]=[C:32]([CH:48]=[CH:49][CH:50]=3)[CH2:33][NH:34][C:35]3[CH:47]=[CH:46][C:38]([C:39]([O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:40])=[CH:37][CH:36]=3)[N:3]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 68379697HCID 68379697, compoundHCID 715341855-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine

Product 1

HCID 66549142HCID 66549142, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Under N2 atmosphere, 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (100 mg, 0.31 mmol), tert-butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylamino)benzoate (150 mg, crude), Pd(PPh3)4 (30 mg, 0.026 mmol) and Na2CO3 (150 mg, 1.41 mmol) in 5 mL of water was added in 30 mL of 1,4-dioxane. The mixture was stirred at reflux for 18 hours. The solvent was removed under reduce pressure and the residue was purified by silica gel chromatography, eluting with petroleum ether and ethyl acetate (5:1) to give tert-butyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzylamino)benzoate (72 mg, 41%) as a yellow sold. 1H NMR (300 MHz, DMSO): δ 8.87 (s, 1H), 8.54-8.47 (m, 2H), 7.86-7.82 (m, 3H), 7.49-7.28 (m, 2H), 7.27-7.23 (m, 1H), 6.94 (d, 1H, J=8.7 Hz), 6.65-6.62 (m, 2H), 4.49 (s, 2H), 4.16 (s, 3H), 4.13 (s, 3H). LC-MS: 570 [M+H]+, tR=1.83 min. HPLC: 98.31% at 214 nm, 98.91% at 254 nm, tR=8.06 min.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent was removed
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with petroleum ether and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-36989776d681434a9df9ae835dbe4982
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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