Naphthalen-2-yl-boron → 5-(3,5-Diethoxy-4-naphthalen-2-yl-benzyl)-pyrimidine-2,4-diamine

HRID 2416296Notes

Reaction equation

HRID 2416296 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]=1I)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2].[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[B].C(OC1C=C(CC2C(N)=NC(N)=NC=2)C=C(OCC)C=1C1C=CC=CC=1)C>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]=1[C:25]1[CH:24]=[CH:23][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2]

Participants

4

Reactant 3

HCID 20596918Naphthalen-2-yl-boronHCID 226369195-(3,5-Diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamineHCID 226369825-(2,6-Diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine

Product 1

HCID 226370215-(3,5-Diethoxy-4-naphthalen-2-yl-benzyl)-pyrimidine-2,4-diamine

Procedure

Starting from 5-(3,5-diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (example 1) (414 mg; 1 mmol) and naphthalen-2-yl-boron acid (690 mg; 4 mmol), 327 mg (79%) 5-(2,6-diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine [sic] are obtained as a colourless powder.

Workup

  1. customare obtained as a colourless powder

Sources & evidence

ORD record
ord-ce2369c0cbab4dd8888ee4c1b18fc13b
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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