Sodium Carbonate → HCID 19050464, compound

HRID 1603294Notes

Reaction equation

HRID 1603294 reaction equation
BrC1C=NC(I)=NC=1.C(OC1C=CC(B(O)O)=CC=1)CCCCCCC.C(=O)([O-])[O-].[Na+].[Na+].F[C:34]1[C:39](F)=[C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:37]=[CH:36][C:35]=1[C:50]1[N:55]=[CH:54][C:53]([Br:56])=[CH:52][N:51]=1>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.COCCOC>[CH2:42]([O:41][C:38]1[CH:37]=[CH:36][C:35]([C:50]2[N:55]=[CH:54][C:53]([Br:56])=[CH:52][N:51]=2)=[CH:34][CH:39]=1)[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 70066515-Bromo-2-iodopyrimidineHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 19050464HCID 19050464, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (1.23 g, 4.32 mmol), 4-octyloxyphenylboronic acid 7 (1.33 g, 5.18 mmol), tetrakis(triphenylphosphine)palladium (150 mg, 0.13 mmol), DME (30 ml), aqueous 2M sodium carbonate (30 ml). The experimental procedure was as described for compound 4 to yield the phenylpyrimidine 8 (0.67 g, 43%) (from EtOH), m.p. 95.0° C.; νmax /cm-1 (KBr) 2920, 1605, 1525, 1425, 1260, 1170, 1120 and 790; δ 0.90 (3H, t, Me), 1.20-1.55 (10H, m), 1.84 (2H, quint, OCH2CH2), 4.02 (2H, t, OCH2), 6.97 (2H, d, J 7, 3'- and 5'-H), 8.33 (2H, d, J 7, 2'- and 6'-H) and 8.76 (2H, s, 4- and 6-H); m/z 366 (M+), 364 (M+), 252 (M+ -C8H16) 250 (M+ -C8H16), 195 and 186.

Sources & evidence

ORD record
ord-a5632c0c736044ed8ac462d34485431d
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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