Sodium Carbonate → HCID 67021980, compound

HRID 1665515Notes

Reaction equation

C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)O1.[C:23]([O:27][C:28]([N:30]1[CH2:33][CH:32]([CH2:34][NH:35][C:36]2[N:41]=[C:40](Cl)[N:39]=[C:38]([N:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)[N:37]=2)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>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.C(COC)OC>[C:23]([O:27][C:28]([N:30]1[CH2:33][CH:32]([CH2:34][NH:35][C:36]2[N:41]=[C:40]([C:15]3[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=3)[N:39]=[C:38]([N:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)[N:37]=2)[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

Conditions

Temperature: 140 °C

Procedure

To a microwave processing tube was added dimethoxyethane (15 mL), aqueous Na2CO3 (2 molar)(4 mL, 8 mmol, 2 eq), (Ph3P)4Pd (317 mg, 0.55 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1.81 g, 8.30 mmol, 1.5 eq) and 3-[(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-ylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester (1.3 g, 5.53 mmol) and the vessel was sealed. The mixture was heated to 140° C. for 60 minutes. The solvents were removed and the crude compound was purified by silica gel chromatography using CH2Cl2/Ethyl acetate (10:1) and later CH2Cl2/MeOH/NH3 (15:1:0.1) to give the product as a off-white solid (1.3 g, 53% yield).

Workup

customthe vessel was sealed
customThe solvents were removed
customthe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record: ord-6443bb207d48418f8b84a9b4a2da5f3a
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039469B2

Reaction notes

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