Dibah → 2-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-hydroxynaphthalen-7-yl)-4-pyrimidineamine

HRID 76428

Reaction equation

HRID 76428 reaction equation
C1COC2(N)N(C(NC3C=CC4OC(CO)=CC=4C=3)=NC=C2F)O1.[Cl:25][C:26]1[N:31]=[C:30]([NH:32][C:33]2[CH:42]=[C:41]3[C:36]([CH2:37][CH2:38][CH2:39][C:40]3=[O:43])=[CH:35][CH:34]=2)[C:29]([F:44])=[CH:28][N:27]=1.CC(C[Al]CC(C)C)C>>[Cl:25][C:26]1[N:31]=[C:30]([NH:32][C:33]2[CH:42]=[C:41]3[C:36]([CH2:37][CH2:38][CH2:39][CH:40]3[OH:43])=[CH:35][CH:34]=2)[C:29]([F:44])=[CH:28][N:27]=1

Participants

4

Reactant 3

HCID 16682954DibahHCID 220607872-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-oxonaphthalen-7-yl)-4-pyrimidineamineHCID 66759177N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine

Product 1

HCID 220608542-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-hydroxynaphthalen-7-yl)-4-pyrimidineamine

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-oxonaphthalen-7-yl)-4-pyrimidineamine was reduced with Dibal-H to yield 2-chloro-5-fluoro-N4-(1,2,3,4-tetrahydro-1-hydroxynaphthalen-7-yl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.05 (d, 1H, J=3.0 Hz), 7.59 (d, 1H, J=2.4 Hz), 7.14 (d, 1H, J=8.1 Hz), 6.93 (bs, 1H), 4.82-4.78 (m, 1H), 2.82-2.71 (m, 2H), 2.08-1.74 (m, 5H); 19F NMR (282 MHz, CDCl3): −44661; LCMS: purity: 94%; MS (m/e): 294 (MH+).

Sources & evidence

ORD record
ord-de403ea4ea9b46c7a66bdce1a5a890e5
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Linked notes

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