Sodium Carbonate → HCID 66550548, compound

HRID 1410122Notes

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.[OH:22][CH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[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:28]3[CH:29]=[C:24]([CH2:23][OH:22])[CH:25]=[CH:26][CH:27]=3)[N:3]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 0.62 mmol), 3-(hydroxymethyl)phenylboronic acid (104 mg, 0.68 mmol), Pd2(dba)3 (71 mg, 0.12 mmol), X-Phos (118 mg, 0.25 mmol), Na2CO3 (131 mg, 1.2 mmol) in dioxane (20 mL) and H2O (5 mL) was heated to 90° C. with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by column chromatography (MeOH:DCM=1:80) to give (3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)phenyl)methanol (51 mg, 21%) as yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.84 (s, 1H), 8.49 (s, 1H), 8.42 (d, 1H, J=6.9 Hz), 7.97 (s, 1H), 7.87 (s, 1H), 7.49-7.46 (m, 2H), 7.18 (dd, 1H, J1=8.7 Hz, J2=2.7 Hz), 6.93 (d, 1H, J=8.4 Hz), 4.79 (s, 2H), 4.00 (s, 3H), 3.93 (s, 3H). LC-MS: 395 [M+H]+, tR=1.48 min. HPLC: 98.36% at 214 nm, 98.69% at 254 nm, tR=6.086 min.

Workup

customThe solvent was removed in vacuo
customthe resulting mixture was purified by column chromatography (MeOH:DCM=1:80)

Sources & evidence

ORD record: ord-830d3f9898074213a6f68c6bd0e8dcec
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921383B2

Reaction notes

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